(2S,3S)-N-[(2S)-1-methoxy-1-oxo-3-phenyl-2-propyl]-3-azido-2-hydroxyheptanamide → (2S,3S)-N-[(2S)-1-methoxy-1-oxo-3-phenyl-2-propyl]-3-amino-2-hydroxyheptanamide

HRID 1698441Notes

Reaction equation

HRID 1698441 reaction equation
[CH3:1][O:2][C:3](=[O:25])[C@@H:4]([NH:12][C:13](=[O:24])[C@@H:14]([OH:23])[C@@H:15]([N:20]=[N+]=[N-])[CH2:16][CH2:17][CH2:18][CH3:19])[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1>[C].[Pd].CO>[CH3:1][O:2][C:3](=[O:25])[C@@H:4]([NH:12][C:13](=[O:24])[C@@H:14]([OH:23])[C@@H:15]([NH2:20])[CH2:16][CH2:17][CH2:18][CH3:19])[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

4

Reactant 1

HCID 59655559(2S,3S)-N-[(2S)-1-methoxy-1-oxo-3-phenyl-2-propyl]-3-azido-2-hydroxyheptanamide

Product 1

HCID 59655562(2S,3S)-N-[(2S)-1-methoxy-1-oxo-3-phenyl-2-propyl]-3-amino-2-hydroxyheptanamideYield 94%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

To 30 ml of a methanol solution containing 442 mg (1.27 mmol) of (2S,3S)-N-[(2S)-1-methoxy-1-oxo-3-phenyl-2-propyl]-3-azido-2-hydroxyheptanamide was added 45 mg of 5% palladium carbon, and the mixture was stirred under hydrogen atmosphere for 18 hours. Insoluble materials were filtered off, and the filtrate was distilled under reduced pressure to obtain 385 mg (Yield: 94%) of the title compound.

Workup

  1. filtrationInsoluble materials were filtered off
  2. distillationthe filtrate was distilled under reduced pressure

Sources & evidence

ORD record
ord-430a7a9f1e0946babc589c7a7b8007d3
Source dataset
uspto-grants-2012_04
Patent number
US08163943B2

Reaction notes

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