DL-Serine methyl ester

Stearoyl chloride in dimethylformamide added to DL-serine methyl ester (prepared from the hydrochloride with a soln. of the stoichiometric amount of Na in methanol) in dimethylformamide containing pyridine, and allowed to stand 1 hr. at room temp. N-stearoyl-DL-serine methyl ester. Y 70%. F. e. s. B. Weiss, J. Org. Ghem. 24, 1367 (1959). 

C3H9N3O2 64616-76-8) see Benserazide D-serine methyl ester hydrochloride (C4H,()C N03 5874-57-7) sec Cycloserine A -(DL-seryl)-2,3,4-trihydroxybenzaldehyde hydrazone (CJ0H13N3O5) see Benserazide (-)-shikimic acid... 

Vercellotti and associates121,126 were the first to apply the Helferich -Wedemeyer procedure127 (which uses mercury dicyanide as the acid acceptor) for the preparation of a glycosylamino acid, namely, 3-0-(2-acetamido-3,4,6-tri-0-acetyl-2-deoxy-/ -D-glucopyranosyl)-N-(2,4-di-nitrophenyl)-L-serine and -DL-threonine methyl ester derivatives (162). 

The DL-serine uracil derivative 580 was prepared from OL-serine methyl ester hydrochloride by V-benzoylation to give 578 chloromethylation gave 579, which then was substituted by the silylated uracil (88ZOB2404). 

Figure 10 Images of domains of monolayers of the o-enantiomer, L-enantiomo-, and racemic mixture of A-stearoylserine methyl ester clearing showing chiral discrimination effects. The domains of the enantiomers display unique curvature, and the domain of the racemic mixture shows featnres with both senses of curvature and hence evidence for chiral segregation. Reproduced from Ref. 62. American Chemical Society, 2003, and the figure caption reads as follows Chiral discrimination of the condensed-phase domains of N-stearoyl serine methyl ester monolayers spread on pH 3 water, (a) D-enantiomer (b) L-enantiomer (c) and (d) 1 1 dl racemate. Image size 80 x 80 pm.

Cycloserine has been synthesized by several workers including Stammer and Evans. The method of Evans will be briefly described. Evans reported cycloserine can be synthesized by converting DL-Serine to its methyl ester hydrochloride by Fischer esterification. 

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