HCID 86746276, compound → N2 [3(S)-amino-2(R)-hydroxy-4-phenylbutyl]-N1-tert.butyl-4(S)-hydroxy-L-prolinamide

HRID 54108Notes

Reaction equation

HRID 54108 reaction equation
[N:1]#[N:2].C(OC([NH:13][C@@H:14]([CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[C@H:15]([OH:30])[CH2:16][C@@:17]1([C:27]([NH2:29])=[O:28])[CH2:21][C@H:20]([OH:22])[CH2:19][N:18]1[C:23]([CH3:26])([CH3:25])[CH3:24])=O)C1C=CC=CC=1>C(O)C.[Pd]>[N:1]#[N:2].[NH2:13][C@@H:14]([CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[C@H:15]([OH:30])[CH2:16][C@@:17]1([C:27]([NH2:29])=[O:28])[CH2:21][C@H:20]([OH:22])[CH2:19][N:18]1[C:23]([CH3:26])([CH3:24])[CH3:25]

Participants

4

Reactant 1

HCID 86746276HCID 86746276, compound

Product 1

HCID 86746274N2 [3(S)-amino-2(R)-hydroxy-4-phenylbutyl]-N1-tert.butyl-4(S)-hydroxy-L-prolinamideYield 98.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

0.11 g of N2 -[3(S)-(benzyloxyformamido)-2(R)-hydroxy-4-phenylbutyl]-N1 -tert.butyl-4(S)-hydroxy-L-prolinamide was dissolved in 10 ml of ethanol and hydrogenated over 20 mg 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 0.08 g of N2 -[3(S)-amino-2(R)-hydroxy-4-phenylbutyl]-N1 -tert.butyl-4(S)-hydroxy-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-0b18d76763e04c5f8fecc5af80f19e6c
Source dataset
uspto-grants-1997_04
Patent number
US05620987

Reaction notes

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