Cyclohexanecarboxylic 4-amino

A. cis- and trans-4-Aminocyclohexanecarboxylic acid. A mixture of 27.4 g. (0.20 mole) of />-aminobenzoic acid (Note 1), 200 ml. of water, and 2 g. of 10% rhodium-0.1% palladium on carbon ciitalyst (Note 2) is placed in a pressure bottle and hydrogenated at 50 p.s.i. When 0.6 mole of hydrogen has been absorbed (Note vl), the mixture is filtered and concentrated under reduced pressure until crystals start to form (Note 4). The mixture is diluted with 200 ml. of dimethylformamide and cooled to 5°, filtered, washed with dimethylformamide, then methanol, and [Pg.120]

For more remote substitution p is expected to be smaller. Thus Hay and Porter-28 found p = 0.6 for the alkaline hydrolysis of the methyl esters of a-amino acids, RCH(NH2)COOCH.3 in water at 25°C. However, higher sensitivities are possible if the geometry of the system is such that the direct transmission of polar effects becomes more important. For example, Roberts and Moreland245 found that the effects of substituents in the 4 position of ethyl bicyclo-[2.2.2]octane-l-carboxylates (28) on the hydrolysis in 88% ethanol at 30°C are comparable to those observed for meta- anti para-substituted benzoates (p = 2.24), and a similar, though smaller, effect, is observed for methyl rrarts-4-substituted cyclohexanecarboxylates (29). 

Triethylamine (8) Ethanamine, N,N-diethyl- (9) (121-44-8) p-Toluensulfonyl chloride (8) Benzenesulfonyl chloride, 4-methyl- (9) (98-59-9) (lS,2S)-2-(N-Tosylamino)cyclohexanecarboxylic acid Cyclohexanecarboxylic acid, 2-[[(4-methylphenyl)sulfonyl]amino]-, (1S-trans)- (12) (110456-11-6)... 

The next five procedures of the final set illustrate the important process of preparation of enantiomerically pure materials beginning with readily available enantiomerically pure natural substances. Use of commercially available enantiomerically pure pyrrolobenzodiazepine-5,11-diones to prepare (1S,2S)-(+)-2-(N-TOSYLAMINO)CYCLOHEXANECARBOXYLIC ACID is described in the first procedure. The next preparation illustrates an optimized preparation of DIETHYL (2S,3R)-2-(N-tert-BUTOXYCARBONYL)AMINO-3-HYDROXYSUCCINATE... 

C7H13N02 trans-2-amino-1 -cyclohexanecarboxylic acid 5691-19-0 23.64 1.0259 2 11947 C7H1404 (-)-2,3-0-isopropylidene-D-threitol 73346-74-4 21.50 1.0845 2... 

C7H13N02 cis-2-amino-l -cyclohexanecarboxylic acid 5691-20-3 23.64 1.0259 2 11949 C7H1405 6-deoxy-3-0-methylgalactose 4481-08-7 25.00 1.1180 2... 

Cyclohexanecarboxylic acid, 2,2-dimethyl-2,4-dioxo-3-(1-((2- propenyloxy)amino)butylidene)-, methyl ester, sodium salt Alloxydim-sodium 3633, 4271a ... 

Benzoic acid ethyl ester. See Ethyl benzoate Benzoic acid, 4-(((ethylphenylamino) methylene) amino)-, ethyl ester. See N-(p-Ethoxycarbony I phenyl )-N -ethy l-N -phenylformamidine Benzoic acid, hexahydro-. See Cyclohexanecarboxylic acid Benzoic acid, hexyl ester. See Hexyl benzoate Benzoic acid, 4-hydroxy- Benzoic acid, p-hydroxy-. See 4-Hydroxybenzoic acid Benzoic acid, 2-hydroxy-, butyl ester. See Butyl salicylate... 

Floss and Hu in 2004 reported studies on feeding experiments conducted S. nodosus ssp. asukaensis ATCC 29757 that shed light on the biosynthesis of asukamycin 221. Thus, because 221 is assembled from three components, namely an upper polyketide chain initiated by cyclohexanecarboxylic acid, a lower polyketide chain initiated by the mC-j starter unit, and a cyclized 5-aminolevulinic acid moiety, 2-amino-3-hydroxycyclopent-2-enone (C5N unit) 232, it was logical to expect that these are synthesized separately from their respective precursors and are then assembled into the complete molecular framework. To try to elucidate in which order these building blocks are assembled, the various components and partial assemblies of components were synthesized in labeled form, reported in Figure 3.73, and the ones that are incorporated into the final product asukamycin 221 were determined [259]. 

Nitrilases suitable for the transformations of alicyclic five- and six-membered y-amino nitriles were selected from the set of commercial nitrilases available from BioCatalytics Inc. (now Codexis) [59] and the effects of the substrate structure (ring size, protecting group, and trans versus cis configuration) were studied. N-tosylated derivatives of cis-3-amino cydopentane- and cyclohexanecarboxylic acids were obtained with the highest enantiopurities. Production of N-substituted pyrrolidine-and piperidinecarboxylic acids was also possible using the same nitrilases, but the enantiopurities of these products were generally low [60]. 

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