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

HRID 1757767Notes

Reaction equation

HRID 1757767 reaction equation
[N:1]#[N:2].C(OC([NH:13][C@@H:14]([CH2:38][C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)[C@H:15]([OH:37])[CH2:16][C@@:17]1([C:34]([NH2:36])=[O:35])[CH2:21][C@@H:20]([NH:22][C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:19][N:18]1[C:30]([CH3:33])([CH3:32])[CH3:31])=O)C1C=CC=CC=1>C(O)C.[Pd]>[N:1]#[N:2].[NH2:13][C@@H:14]([CH2:38][C:39]1[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=1)[C@H:15]([OH:37])[CH2:16][C@@:17]1([C:34]([NH2:36])=[O:35])[CH2:21][C@@H:20]([NH:22][C:23]([O:25][C:26]([CH3:29])([CH3:27])[CH3:28])=[O:24])[CH2:19][N:18]1[C:30]([CH3:31])([CH3:32])[CH3:33]

Participants

4

Reactant 1

HCID 86746290N2 [3(S)-(benzyloxyformamido)-2(R)-hydroxy-4-phenylbutyl]-4(R)-(tert.butoxyformamido)-N1-tert.butyl-L-prolinamide

Product 1

HCID 86746288N2 [3(S)-amino-2(R)-hydroxy-4-phenylbutyl]-4(R)-(tert.butoxyformamido)-N1-tert-butyl-L-ProlinamideYield 99%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

0.22 g of N2 -[3(S)-(benzyloxyformamido)-2(R)-hydroxy-4-phenylbutyl]-4(R)-(tert.butoxyformamido)-N1 -tert.butyl-L-prolinamide was dissolved in 10 ml of ethanol and hydrogenated over 0.05 g of 10% palladium-on-carbon at room temperature and under atmospheric pressure for 2 hours. The catalyst was filtered off and the filtrate was evaporated to give 0.17 g of N2 -[3(S)-amino-2(R)-hydroxy-4-phenylbutyl]-4(R)-(tert.butoxyformamido)-N1 -tert.butyl-L-prolinamide as a gum which was used without further purification.

Workup

  1. filtrationThe catalyst was filtered off
  2. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-087284a098e94b49abfa22d85aed7be2
Source dataset
uspto-grants-1995_08
Patent number
US05446161

Reaction notes

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