3(R,S)-methoxymethyl-1,2,3,4-tetrahydroquinoline → 5(S)-Amino-4(S)-hydroxy-2(R),7,7-trimethyl-8-[3(R,S)-methoxymethyl-1,2,3,4-tetrahydroquinolin-1-ylcarbonyl]-octanoic acid (N-butyl)amide

Participants

Reaction Steps

Starting from 300 mg of 3-[N-tert-butoxycarbonyl-4(S)-(3-carboxy-2,2-dimethylpropyloxy-2,2-dimethyl-1,3-oxazolidin-5(S)-yl]-2(R)-methyl-propionic acid (N-butyl)amide and 465 mg of 3(R,S)-methoxymethyl-1,2,3,4-tetrahydroquinoline and subsequent reaction of the (4O,5N-isopropylidene)-5(S)-tert-butoxycarbonylamino-4(S)-hydroxy-2(R),7,7-trimethyl-8-[3(R,S)-methoxymethyl-1,2,3,4-tetrahydroquinolin-1-ylcarbonyl]-octanoic acid (N-butyl)amide obtained (in a manner analogous to that described in Example 1a); Rf (A)=0.38), by the method described in Example 1), the title compound is obtained as a diastereomer mixture: Rf (S)=0.31; FAB-MS: (M+H)+ =476.

Provenance & Evidence