Sequential treatment

The MauIg Color Reaction. The procedure for this test consists basically of three sequential treatments of lignified material with 1% potassium permanganate, 3% hydrochloric acid, and concentrated ammonium hydroxide. A red-purple color develops for hardwoods and a brown color... 

Treatment of quinoline with cyanogen bromide, the von Braun reaction (17), in methanol with sodium bicarbonate produces a high yield of l-cyano-2-methoxy-l,2-dihydroquinoline [880-95-5] (5) (18). Compound (5) is quantitatively converted to 3-bromoquinoline [5332-24-1], through the intermediate (6) [66438-70-8]. These conversions are accompHshed by sequential treatment with bromine in methanol, sodium carbonate, or concentrated hydrochloric acid in methanol. Similar conditions provide high yields of 3-bromomethylquinoHnes. 

Dihydroxyquiaolines are found ia nature and may be prepared synthetically. Heating 3,l-benzoxazia-4-ones with strong base or sequential treatment of A/-acetoacetylanthranilate with base, then acid, produce 2,4-dihydroxyquiQolines [70254-43-2] (127,128). An enzymatic preparation of 4,5-dihydroxyquiQoline has been reported (129). 

Beecham P-lactamase iiihibitoi BRL 42715 [102209-75-6] (89, R = Na), C IlgN O SNa (105). Lithium diphenylamide, a weaker base, was used to generate the anion of (88) which on sequential treatment with l-methyl-l,2,3-ttia2ole-4-carbaldehyde and acetic anhydride gives a mixture of diastereomers of the bromoacetate (90). Reductive elimination then provided the (Z)-penem (89, R = d5 Q [ OC15 -p) as major product which on Lewis acid mediated deprotection gave BRL 42715 (89, R = Na). 

List the appropriate codes for the treatment steps in the order that they occur (in column B) and then put an "X" in the boxes in column D for all these sequential treatment steps. 

An example of how to use the sequential treatment option is provided in Appendix C. 

This column requires you to indicate "Yes or "No" to whether the treatment efficiency estimate is based on actual operating data. For example, you would check Yes if the estimate is based on monitoring of influent and effluent wastes under typical operating conditions. For sequential treatment, do not indicate "Yes" or "No" in column F for a treatment step unless you have provided a treatment estimate in column E. 

All sequential treatment steps must be indicated for the metal compound categories reported even if the treatment method does not affect the particular metal. For example, ionic exchange must be reported as a treatment method for lead, zinc, chromium, and selenium compounds, oven though the method affects only the selenium compound. 

Air Treatment Systems. Fabric filters and cyclone collectors are considered to be mechanical separation systems the treatment code for these systems is A06. The treatment code for wet scrubbers is A03. Information on each air treatment system must be entered individually in Section 7. The cyclone collector and fabric filter on the lead oxide mill exhaust are sequential treatment systems, because they treat the same wastestream in sequence. Therefore, sequential treatment must be indicated for both systems in column D of Section 7. You are required to indicate the influent concentration only to... 

Perfluorohexamethylbenzene is converted to perfluoropentamethylbenzoic acid by sequential treatment with sodium methoxide, then concentrated sulfuric acid, and finally fuming sulfuric acid [37] (equation 38). The intermediate methyl ortho ester and methyl ester of the acid can be isolated... 

The first use of chiral oxazolines as activating groups for nucleophilic additions to arenes was described by Meyers in 1984. " Reaction of naphthyloxazoline 3 with phenyllithium followed by alkylation of the resulting anion with iodomethane afforded dihydronaphthalene 10 in 99% yield as an 83 17 mixture of separable diastereomers. Reductive cleavage of 10 by sequential treatment with methyl fluorosulfonate, NaBKi, and aqueous oxalic acid afforded the corresponding enantiopure aldehyde 11 in 88% yield. 

Meyers has demonstrated that chiral oxazolines derived from valine or rert-leucine are also effective auxiliaries for asymmetric additions to naphthalene. These chiral oxazolines (39 and 40) are more readily available than the methoxymethyl substituted compounds (3) described above but provide comparable yields and stereoselectivities in the tandem alkylation reactions. For example, addition of -butyllithium to naphthyl oxazoline 39 followed by treatment of the resulting anion with iodomethane afforded 41 in 99% yield as a 99 1 mixture of diastereomers. The identical transformation of valine derived substrate 40 led to a 97% yield of 42 with 94% de. As described above, sequential treatment of the oxazoline products 41 and 42 with MeOTf, NaBKi and aqueous oxalic acid afforded aldehydes 43 in > 98% ee and 90% ee, respectively. These experiments demonstrate that a chelating (methoxymethyl) group is not necessary for reactions to proceed with high asymmetric induction. 

The Ciamician-Dennstedt reaction is currently the only way to date to make calix[4]pyridine 20.(Scheme 8.3.6) Four sequential treatments of calix[4]pyrrole 19 with sodium trichloroacetate results in all four possible geometric isomers of 20 (all four... 

In a useful extension to the Meth-Cohn quinoline synthesis, pyridoquinolin-2-ones 27 are readily prepared in a one-pot procedure by sequential treatment of an acetanilide 3, firstly with the Vilsmeier reagent from DMF and POCI3 to afford the intermediate 16, which is then further reacted in situ with another secondary amide. ... 

In addition, several progestins have been used in the absence of estrogens for purposes of contraception. It is clear that they owe their efficacy, which is not as high as that of the combination or sequential treatments, to some mechanism other than inhibition of ovulation. These are not yet represented by marketed entities for that indication. 

The synthesis of key intermediate 12, in optically active form, commences with the resolution of racemic trans-2,3-epoxybutyric acid (27), a substance readily obtained by epoxidation of crotonic acid (26) (see Scheme 5). Treatment of racemic 27 with enantio-merically pure (S)-(-)-1 -a-napthylethylamine affords a 1 1 mixture of diastereomeric ammonium salts which can be resolved by recrystallization from absolute ethanol. Acidification of the resolved diastereomeric ammonium salts with methanesulfonic acid and extraction furnishes both epoxy acid enantiomers in eantiomerically pure form. Because the optical rotation and absolute configuration of one of the antipodes was known, the identity of enantiomerically pure epoxy acid, (+)-27, with the absolute configuration required for a synthesis of erythronolide B, could be confirmed. Sequential treatment of (+)-27 with ethyl chloroformate, excess sodium boro-hydride, and 2-methoxypropene with a trace of phosphorous oxychloride affords protected intermediate 28 in an overall yield of 76%. The action of ethyl chloroformate on carboxylic acid (+)-27 affords a mixed carbonic anhydride which is subsequently reduced by sodium borohydride to a primary alcohol. Protection of the primary hydroxyl group in the form of a mixed ketal is achieved easily with 2-methoxypropene and a catalytic amount of phosphorous oxychloride. 

Ketone 13 possesses the requisite structural features for an a-chelation-controlled carbonyl addition reaction.9-11 Treatment of 13 with 3-methyl-3-butenylmagnesium bromide leads, through the intermediacy of a five-membered chelate, to the formation of intermediate 12 together with a small amount of the C-12 epimer. The degree of stereoselectivity (ca. 50 1 in favor of the desired compound 12) exhibited in this substrate-stereocontrolled addition reaction is exceptional. It is instructive to note that sequential treatment of lactone 14 with 3-methyl-3-butenylmagnesium bromide and tert-butyldimethylsilyl chloride, followed by exposure of the resultant ketone to methylmagnesium bromide, produces the C-12 epimer of intermediate 12 with the same 50 1 stereoselectivity. 

All that remains before the final destination is reached is the introduction of the C-l3 oxygen and attachment of the side chain. A simple oxidation of compound 4 with pyridinium chlorochro-mate (PCC) provides the desired A-ring enone in 75 % yield via a regioselective allylic oxidation. Sodium borohydride reduction of the latter compound then leads to the desired 13a-hydroxy compound 2 (83% yield). Sequential treatment of 2 with sodium bis(trimethylsilyl)amide and /(-lactam 3 according to the Ojima-Holton method36 provides taxol bis(triethylsilyl ether) (86 % yield, based on 89% conversion) from which taxol (1) can be liberated, in 80 % yield, by exposure to HF pyridine in THF at room temperature. Thus the total synthesis of (-)-taxol (1) was accomplished. 

Sequential treatment of oxamoyl chloride 495 with imidrazones and then with perchloric acid and acetic anhydride gave 496 (86S635) (Scheme 103). 

The sequential treatment of triazine derivative 990 with acyl chlorides and acetic anhydride and perchloric acid afforded (86H1031) thiadi-azolo[l, 2,4]triazinium perchlorates 991. On the other hand, cyclocondensation of 992 with organic acids gave 993 [82JHC1577 83JAP(K)58/180492] and 994 with aromatic aldehydes (84JIC552) (Scheme 183). 

Jacobsen has utilized [(salen)Co]-catalyzed kinetic resolutions of tenninal epoxides to prepare N-nosyl aziridines with high levels of enantioselectivity [72], A range of racemic aryl and aliphatic epoxides are thus converted into aziridines in a four-step process, by sequential treatment with water (0.55 equivalents), Ns-NH-BOC, TFA, Ms20, and carbonate (Scheme 4.49). Despite the apparently lengthy procedure, overall yields of the product aziridines are excellent and only one chromatographic purification is required in the entire sequence. 

Meth-Cohn has developed an efficient one-pot synthesis of isatins 108 by the sequential treatment of iV-substituted formanilides 107 with oxalyl chloride, Hunig s base, and bromine... 

Treatment of N-benzoyl-L-alanine with oxalyl chloride, followed by methanolic triethylamine, yields methyl 4-methyl-2-phenyloxazole-5-carboxylate 32 <95CC2335>. a-Keto imidoyl chlorides, obtained from acyl chlorides and ethyl isocyanoacetate, cyclise to 5-ethoxyoxazoles by the action of triethylamine (e.g.. Scheme 8) <96SC1149>. The azetidinone 33 is converted into the oxazole 34 when heated with sodium azide and titanium chloride in acetonitrile <95JHC1409>. Another unusual reaction is the cyclisation of compound 35 to the oxazole 36 on sequential treatment with trifluoroacetic anhydride and methanol <95JFC(75)221>. 

Shi M, Wang RS, Zhang H, Zhu YF, Han B, Zhang Y, Jin LJ, Yang ZJ, Xu YP (2006) Sequential treatment with lamivudine and interferon-alpha monotherapies in hepatitis B e antigennegative Chinese patients and its suppression of lamivudine-resistant mutations, J Antimicrob Chemother 58 1031-1035... 

These phosphinous amide anions are presumably responsible for the formation of the by-products AT-phosphino phosphinous amides 11 and mono-phosphazenes derived from diphosphanes 12 in the sequential treatment of primary amines with n-BuLi and chlorophosphanes for preparing NH phosphinous amides [75,88] (Scheme 14). Compounds 11 and 12 are presumably derived from anions 9 and 10, respectively, generated by deprotonation of the newly formed phosphinous amide with the lithiated amine R NHLi. In solution, 9 can establish a metallotropic equilibrium with 10. 

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