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

Participants

Reaction Steps

Starting from 230 mg of 3-[N-tert-butoxycarbonyl-4(S)-(3-carboxy-2,2-dimethylpropyl)-2,2-dimethyl-1,3-oxazolidin-5(S)-yl]-2(R)-methyl-propionic acid (N-butyl)amide and 287 mg of 3(R,S)-methoxyethyl-1,2,3,4-tetrahydroquinoline via (4O,5N-isopropylidene)-5(S)-tert-butoxycarbonylamino-4(S)-hydroxy-2(R),7,7-trimethyl-8-[3(R,S)-methoxyethyl-1,2,3,4-tetrahydroquinolin-1-ylcarbonyl]-octanoic acid (N-butyl)amide (analogously to Example 1a); Rf (A)=0.17; Rt (VI)=35.8 min) and 5(S)-tert-butoxycarbonylamino-4(S)-hydroxy-2(R),7,7-trimethyl-8-[3(R,S)-methoxyethyl-1,2,3,4-tetrahydroquinolin-1-ylcarbonyl]-octanoic acid (N-butyl)amide (Rf (V)=0.81; Rt (VI)=31.0 min) in a manner analogous to that described in Example 1) as a diastereomer mixture: Rf (V)=0.44; Rt (VI)=23.6 min; FAB-MS: (M+H)+ =490.

Provenance & Evidence