N2 [3(S)-(benzyloxyformamido)-2(R)-hydroxy-4-phenylbutyl]-N1-phenyl-L-prolinamide → N2 [3(S)-amino-2(R)-hydroxy-4-phenylbutyl]-N1-phenyl-L-prolinamide

HRID 742852Notes

Reaction equation

HRID 742852 reaction equation
[N:1]#[N:2].C(OC([NH:13][C@@H:14]([CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)[C@H:15]([OH:31])[CH2:16][C@@:17]1([C:28]([NH2:30])=[O:29])[CH2:21][CH2:20][CH2:19][N:18]1[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=O)C1C=CC=CC=1>C(O)C.[Pd]>[N:1]#[N:2].[NH2:13][C@@H:14]([CH2:32][C:33]1[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1)[C@H:15]([OH:31])[CH2:16][C@@:17]1([C:28]([NH2:30])=[O:29])[CH2:21][CH2:20][CH2:19][N:18]1[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

4

Reactant 1

HCID 86746224N2 [3(S)-(benzyloxyformamido)-2(R)-hydroxy-4-phenylbutyl]-N1-phenyl-L-prolinamide

Product 1

HCID 86746222N2 [3(S)-amino-2(R)-hydroxy-4-phenylbutyl]-N1-phenyl-L-prolinamideYield 94.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 0.45 g of N2 -[3(S)-(benzyloxyformamido)-2(R)-hydroxy-4-phenylbutyl]-N1 -phenyl-L-prolinamide in 20 ml of ethanol was hydrogenated over 10% palladium-on-carbon for 4 hours to give 0.315 g of N2 -[3(S)-amino-2(R)-hydroxy-4-phenylbutyl]-N1 -phenyl-L-prolinamide in the form of a white solid; MS: m/e 354 [M+H]+.

Sources & evidence

ORD record
ord-53ee31d0d0c543af907fc632d9bbff26
Source dataset
uspto-grants-1996_09
Patent number
US05554756

Reaction notes

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