N2 [3(S)-(benzyloxyformamido)-2(R)-hydroxy-4-phenylbutyl]-N1-tert.butyl-4(R)-hydroxy-L-prolinamide → HCID 86746268, compound

HRID 1757763Notes

Reaction equation

HRID 1757763 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 86746272N2 [3(S)-(benzyloxyformamido)-2(R)-hydroxy-4-phenylbutyl]-N1-tert.butyl-4(R)-hydroxy-L-prolinamide

Product 1

HCID 86746268HCID 86746268, compoundYield 96%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

0.226 g of N2 -[3(S)-(benzyloxyformamido)-2(R)-hydroxy-4-phenylbutyl]-N1 -tert.butyl-4(R)-hydroxy-L-prolinamide was dissolved in 20 ml of ethanol and hydrogenated over 40 mg of 10% palladium-on-carbon at room temperatureand under atmospheric pressure for 2 hours. The catalyst was removed by filtration and the filtrate was evaporated to give 0.16 g of N2 -[3(S)-amino-2(R)-hydroxy-4-phenylbutyl]-N1 -tert.butyl-4(R)-hydroxy-L-prolinamide as a gum which was used without further purification.

Workup

  1. customThe catalyst was removed by filtration
  2. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-a3f297bc34ce4205bac0839f2195eec3
Source dataset
uspto-grants-1995_08
Patent number
US05446161

Reaction notes

Loading…