Preparing an amino acid derivative, comprises reacting carbonyl compound and amine compound, reacting obtained nitrogen containing carbonyl compound with aziridine compound and converting obtained compound to a carbonyl derivative

摘要

Preparation of 2,4-disubstitutedgamma -amino acid derivative (II), comprises reacting carbonyl compound (III) and an amine compound (IV) to give a nitrogen containing carbonyl compound (V) and further reacting (V) with a aziridine compound (VI) to give a nitrogen containing carbonyl compound (VIII) and converting (VIII) to a carbonyl derivative. Preparation of an 2,4-disubstitutedgamma -amino acid derivative of formula (H2N-CH(R1)-CH(R2)-CH(R3)-COOH) (II), comprises either reacting carbonyl compound of formula ((R1)-CH2-C(=O)-X) (III) and an amine compound of formula (R1a)-NH-(Raux) (IV) to give a nitrogen containing carbonyl compound of formula (R1)-CH2-C(=O)-N(R1a)(Raux) (V) and further reacting (V) with a aziridine compound of formula (VI) to give a nitrogen containing carbonyl compound of formula (Pg)N-CH(R1)-CH(R2)-*CH(R3)-C(=O)-N(R1a)(Raux) (VIII) and converting (VIII) to a carbonyl derivative of formula (Pg)N-CH(R1)-CH(R2)-CH(R3)-C(=O)(OR) (IX) or reacting (VI) with a hydroxy containing compound of formula (X). R1alkyl, alkenyl, alkynyl, heteroalkyl, heteroalkenyl, heteroalkynyl, cycloalkyl, heterocycloalkyl or (hetero)aryl (all optionally substituted) or H, preferably methyl, ethyl, propyl or iso-propyl; R2R1, preferably H; R3R1, preferably substituted benzyl or alkyl; Raux : chiral alkyl, aryl, cycloalkyl, heteroalkyl or heterocycloalkyl; R1a : optionally chiral alkyl, aryl, cycloalkyl, heteroalkyl or heterocycloalkyl; R2a : not defined; X : leaving group e.g. a halogen or ester; OR : OH, O-alkyl, O-aryl or O-cycloalkyl, where OR is optionally saponified; and Pg : protection group, which is cleaved, preferably tert-butyloxycarbonyl, allyloxycarbonyl, tosyl, p-nitro-tosyl, benzyloxycarbonyl, 9H-fluoren-9-ylmethoxycarbonyl, trifluoroacetyl, trifluoromethylsulfonyl or methyl sulfonyl. [Image].