摘要 |
(1) Naphthylpropionamide derivs. of formula (I) as dd-, ld-, dl or ll-isomers or (dd+ld) or (dl+ll) mixts. are new. R1 = 1-6C alkyl; R2 = H, halogen, SH, 1-6C alkylthio, PhS, PhCH2S, 1-6C alkylsulphonyl, or PhSO2, opt. ring substd. by halogen or 1-6C alkyl; R4 = CHR5-CH2OH or CH2-CHR6-OH; R5 = 1-6C alkyl, 1-4C p-hydroxyalkyl, HSCH2, MeSC2H4, Ph, HOC6H4, PhCH2, HOC6H4CH2, naphthyl, indolyl or imidazolyl; R6 = 1-6C alkyl, Ph, HOC6H4, (HO)2C6H3 or 4-HO-3-MeOC6H3. (2) Optical resolution of a racemic mixt. of alpha-naphthylpropionic acids of formula (II; R3 = OH) comprises reaction with R4NH2 in an organic solvent contg. a catalytic amt. of a strongly alkaline agent at room temp. to b.pt. to give a (d,d+ld) or (dl+ll) mixt. of (I). R3 = OH, 1-8C alkoxy (opt. substd. by Ph and/or OH), 2-6C aliphatic acyloxy, opt. substd. benzoyloxy, sulphonyloxy, 1,6C alkylsulphonyloxy, benzenesulphonyloxy, 4-methylbenzenesulphonyloxy, 2-imidazolylcarbonyloxy or halogen. Then the diastereoisomeric pair of (I) cpds. is dissolved in a hot solvent and the soln. is gradually cooled until complete pptn. of the less soluble single diastereoisomer occurs. A strong alkali may be present. Then the amide is subjected to acid hydrolysis to give the free acid (II; R3 = OH). Prods. in which R2 = H may be obtd. by catalytic hydrogenation, and when the catalytic hydrogenation is applied to a diastereoisomeric amide pair, a sepn. of the single amide in which R2 = H occurs.
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