2-Amino-3-mcthyl

A mixture of 5-chloro-2-[chloroacetyl(mcthyl)amino]benzophenone (1.136 g, 3.1 mmol), hexamethylenetetramine (1.0 g, 7 mmol) and EtOH (15 mL) was heated under reflux for 10 h. The solvent was distilled off under reduced pressure, H20 (10 mL) was added to the residue and the mixture was extracted with benzene (3 x 10 mL). The combined extracts were washed with H20, dried (Na2S04) and evaporated in vacuo. Crystallization the residue (Et2Q) gave the product yield 0.79g (80%) mp 128-130 C. 

The Ugi reaction has been successfully applied to the synthesis of oligopeptide derivatives, c.g.. in the construction of a pure tetra-L-valine derivative69. The 2-methylpropanaldimine 2 of (/7)-l-ferroccnyl-2-rnethylpropylarnine with /V-formyl-L-2-amino-3-methylbulanoic acid (3) as the carboxylic acid component and methyl A/-[(.S)-2-isocyano-3-mcthyl-l -nxo-buLyl -L-2-aiuino-3-inethylbutanoate (4) furnishes the diastereomeric valyl-valyl-valyl-valine derivatives in a ratio (S,S[R],S,S)i(S,R[R],S,S) of 91 9. The stereoselectivity of the process can be enhanced to 98.5 1.5 when two equivalents of tetraethylammonium A -formylvalinate are added. 

Pyran, tetrahydro-, 3 chloro 2 methyl [2H Pyran, tetrahydro, 3 chloro-2-mcthyl ], cis, trans mixture, 55, 64 2-PYRAZOLIN-5-ONES, 3-alkyl-, 55, 73 2-Pyrazolin 5-one, 3-(l-propyl)-, 55, 73 Pyridine, 2-amino-, p-bromination of, 55, 23... 

Amino-2-methyl-1,1 -dideutero- 111 2-Amino-i-(3,4-methylendioxy-phenyl)- 80 1 -Amino-2 -(2 -mcthyl-propyloxy)- 472 2-Amino-l-oxo-l-phenyl- 325 1 -Amino-1 -phenyl -... 

Amino- 522, 685 4-Amino- 478, 684f., 783 4-(2-Amino-athyl)- 115 2-Amino-4-mcthyl- 686 4-Benzyl-... 

CN [6/ -[6ct.7p(Z)]]-7-[[(2-amino-4-thiazolyl)(methoxyimino)acetyI]aniino]-8-oxo-3-[[(l,2,5,6-tetrah)/dro-2-mcthyl-5,6-dioxo-l,2,4-triazin-3-yl)thio]methyl]-5-thia-l-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid... 

CN 3-[(4-amino-2-methyl-5-pyrimidinyl)mcthyl]-5-(2-hydroxyethyl)-4-methylthiazolium chloride monohydrochloride... 

C7H22N2 140-80-7) see Chloroquinc Mepacnne 7(77)-amino-3-[[(2,5-dihydro-6-hydroxy-2-methyl-5-oxo-l,2,4-triazin-3-yl)thio]mcthyl]-3-cephem-4-carboxylicadd (C12H13N5O5S2 58909-56-1) see Ceftriaxone (15-franx)-l-amino-2,3-dihydro-l//-inden-2-ol (CyH NO 163061-74-3) see Indinavir sulfiite cis-l-amino-2,3-dihydro-l//-inden-2-ol (C9H11NO 7480-35-5) see Indinavir sulfate... 

Hrdlicka PJ, Babu BR, Sorensen MD, Wengel J (2004) Interstrand communication between 2- V-(pyicn-1 -yl)mcthyl-2-amino-LNA monomers in nucleic acid duplexes directional control and signalling of full complementarity. Chem Commun 1478-1479... 

Compound 7-ethyl-7-methyl-3-phenyl-2,3,4,9-tetrahydropyrimido[l,2-tf][l,3,5]triazine-6,8-dione 71 <2002JHC663> was prepared by the one-pot condensation reaction of 6-amino-3-cthyl-3-mcthyl-5//-pyndinc-2,4-dionc 70 with aromatic amines and formaldehyde (Equation 3). 

Aryl-7-(4 -diethylamino-2 -methylphenyl)imino-6-methyl-pyrazolo[5,1-r] [1,2,4]triazoles 57 <2002ARK133> 7-ben-zylidenc-6-mcthyl-3-phenylimino-2//-pyrazolo[5,l-r [ 1,2,4]triazole 58 and 6-benzylidene-6-methyl-2-phenyl-3-phenyli-minopyrazolo[5,l -z][ 1,2,4]triazoIe 59 < 1998PS( 134/135)119> 3-phenyIamino(l//)pyrazolo[5,l -r 1,2,4]triazol-6-oI 60 and l-phenyl-3-phenylamino(l//)pyrazolo[5,l-r][l,2,4]triazol-6-ol 61 <1999EJC175> 6-amino-7-cyano-3-phenylpyra-... 

The ring closure of 2-[iV-(2-hydroxyethyl)-Ar-mcthyl ]amino[ l, 2,41 triazolo[ 1,5-zz] pyrimidin-5-ones 333, promoted by PPA, gives the major compounds 36 and minor amounts of the isomeric derivatives 334 (Equation 59) <2002JHC319>. 

Similarly, the reaction of 4-amino-l-mcthyl-3-methylthio-l//-[l,2,4]tnazol-5(4//)-onc 116 furnishes 6-aryl-2-methyl-7//-[l,2,4]triazolo[4,3-/d[l,2,4]triazol-3(2//)-ones 117 (Equation 32) <1985BCJ735> and the 4-amino[l,2,4]triazole-5(4//)-thione 118 furnishes 6-aryl-l,3-dimethyl-l//-[l,2,4]triazolo[4,3-3][l,2,4]triazoles 119 (Equation 33)... 

Micelle-forming copper complexes were found to effectively discriminate between enantiomers in the hydrolysis of a-amino esters (257). Hydrolysis of (.V)-phenylalanine p-nitrophenyl ester is 14-fold faster than its enantiomer, Eq. 223. Leucine affords 10-fold faster hydrolysis. The authors note that the micellar nature of these systems is extremely important for both rate of hydrolysis and selectivity (258). For example, the /V-mcthyl-dcrivcd ligand 419b leads to inhibition of the hydrolysis process, relative to catalysis by Cu(II) ion alone. 

The enzyme can also catalyze the transfer of an acetyl group from an N-acetylated hydroxylamine (hydroxamic acid) to form an acetoxy product, i.e., an N to O transacetylation and this pathway does not require acetyl Co-A (12). A-hydroxy-4-acetylaminobiphenyl provides an example of this conversion as shown in Figure 7.7. The significance of this pathway is that it leads to the activation of the hydroxamic acid because acetoxy derivatives of aromatic amines are chemically reactive and many are carcinogens such as the heterocyclic amines formed when meat is heated to a high temperature, e.g., 2-amino-1-mcthyl-6-phenylirnidaz()[4,5-i ]pyri(linc. 

The 3-amino-1 -mcthyl-5//-pyrido[4,3-b]indolc derivatives (31 Trp-P-1) and (32 Trp-P-2) were found as tryptophane pyrolysates in broiled fish and meat and in pyrolysates of protein and amino acids by Sugimura and coworkers198. These mutagens are heterocyclic amines and exhibit mutagenicity in the Ames test supplemented with S-9 mix198. The pyridoindole derivatives Trp-P-1 and Trp-P-2 are /V-hydroxylated at the exocyclic amino group to form proximate reactive compounds. 

In contrast, when a twofold excess of the dialkoxydihydropyrazine is used, then 2 1 adducts are obtained. This has been demonstrated18 by reacting A,7V-bis(2-iodoethyl)-4-methylben-zenesulfonamide with two equivalents of the lithiated D-valine/alanine-based dialkoxydihydropyrazine 8 to give 7V.fV-bis 2-[(2S,57 )-2,5-dihydro-5-isopropyl-3,6-dimethoxy-2-mcthyl-2-pyrazinyl]ethyl -4-methylbenzenesulfonamide (9) in high yield and >95% de. The adduct can be hydrolyzed in high yield to the corresponding amino acid methyl ester 10. 

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