HCID 21180635, compound → HCID 57149393, compound

HRID 1386739Notes

Reaction equation

HRID 1386739 reaction equation
[Si]([O:8][CH2:9][C@@H:10]1[C@@H:14]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:13][NH:12][CH2:11]1)(C(C)(C)C)(C)C.O[CH:22]([CH2:35][CH:36]1[CH2:39][CH2:38][CH2:37]1)[C:23]([O:25][CH2:26][C:27]1[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[CH:29][CH:28]=1)=[O:24]>>[OH:8][CH2:9][C@@H:10]1[C@@H:14]([C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH2:13][N:12]([C@@H:22]([CH2:35][CH:36]2[CH2:39][CH2:38][CH2:37]2)[C:23]([O:25][CH2:26][C:27]2[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[CH:29][CH:28]=2)=[O:24])[CH2:11]1

Participants

3

Reactant 2

HCID 21180635HCID 21180635, compoundHCID 21341073(3R,4S)-3-({[tert-butyl(dimethyl)silyl]oxy}methyl)-4-phenylpyrrolidine

Product 1

HCID 57149393HCID 57149393, compound

Procedure

The title compound was prepared from 3-(R)-(t-butyldimethylsilyloxymethyl)-4-(S)-phenyl pyrrolidine (from EXAMPLE 1, Step E) and (R/S)-2-hydroxy-3-(cyclobutyl)propanoic acid (from EXAMPLE 92, Step A) using procedures analogous to those described in EXAMPLE 1, Steps G an H. The diastereomers were separated by HPLC in the second step using the following conditions: Chiralpak AD 2×25 cm column, 17:3 v/v hexanes/iPrOH, 9.0 mL/min, 220 nm) to provide the title compound.

Workup

  1. customThe diastereomers were separated by HPLC in the second step

Sources & evidence

ORD record
ord-22306504f626452eb1630f7cf4cf7a18
Source dataset
uspto-grants-2001_07
Patent number
US06265434B1

Reaction notes

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