4-(Methoxy)benzyl 2-(S)-hydroxy-3-(cyclobutyl)propanoate → 2-(r)-(3-(r)-Formyl-4-(s)-phenylpyrrolidin-1-yl)-3-(cyclobutyl)propanoic acid, 4-(methoxy)benzyl ester

HRID 1386687Notes

Reaction equation

HRID 1386687 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[C@@H: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]>>[CH: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)=[O:8]

Participants

3

Reactant 2

HCID 206724394-(Methoxy)benzyl 2-(S)-hydroxy-3-(cyclobutyl)propanoateHCID 21341073(3R,4S)-3-({[tert-butyl(dimethyl)silyl]oxy}methyl)-4-phenylpyrrolidine

Product 1

HCID 538372272-(r)-(3-(r)-Formyl-4-(s)-phenylpyrrolidin-1-yl)-3-(cyclobutyl)propanoic acid, 4-(methoxy)benzyl ester

Procedure

The title compound was prepared from 3-(R)-(t-butyldimethylsilyloxymethyl)-4-(S)-phenylpyrrolidine (from EXAMPLE 1, Step E) and 4-(methoxy)benzyl 2-(S)-hydroxy-3-(cyclobutyl)propanoate (from EXAMPLE 19, Step E) using procedures analogous to those described in EXAMPLE 1, Steps G-I.

Sources & evidence

ORD record
ord-610f5d23ced44398a8cf1f68d1944935
Source dataset
uspto-grants-2001_07
Patent number
US06265434B1

Reaction notes

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