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

HRID 54095Notes

Reaction equation

HRID 54095 reaction equation
[N:1]#[N:2].C(OC([NH:13][C@@H:14]([CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[C@H:15]([OH:29])[CH2:16][C@@:17]1([C:26]([NH2:28])=[O:27])[CH2:21][CH2:20][CH2:19][N:18]1[C:22]([CH3:25])([CH3:24])[CH3:23])=O)C1C=CC=CC=1>C(O)C.[Pd]>[N:1]#[N:2].[NH2:13][C@@H:14]([CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[C@H:15]([OH:29])[CH2:16][C@@:17]1([C:26]([NH2:28])=[O:27])[CH2:21][CH2:20][CH2:19][N:18]1[C:22]([CH3:25])([CH3:23])[CH3:24]

Participants

4

Reactant 1

HCID 86746263N2 [3(S)-(benzyloxyformamido)-2(R)-hydroxy-4-phenylbutyl]-N1 tert.butyl-L-prolinamide

Product 1

HCID 86746262N2 [3(S)-amino-2(R)-hydroxy-4-phenylbutyl]-N1 tert.butyl-L-prolinamideYield 98.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 0.46 g of N2 -[3(S)-(benzyloxyformamido)-2(R)-hydroxy-4-phenylbutyl]-N1 -tert.butyl-L-prolinamide in 40 ml of ethanol was hydrogenated over 40 mg of 10% palladium-on-carbon at room temperature and under atmospheric pressure for 1.5 hours to give 0.33 g of N2 -[3(S)-amino-2(R)-hydroxy-4-phenylbutyl]-N1 -tert.butyl-L-prolinamide as a gum which crystallized on standing.

Sources & evidence

ORD record
ord-440a0d6f9a854479ba70124f0dca579c
Source dataset
uspto-grants-1997_04
Patent number
US05620987

Reaction notes

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