HCID 90051744, compound → HCID 90051746, compound

HRID 2284704Notes

Reaction equation

HRID 2284704 reaction equation
C([O:8][C:9]1[CH:10]=[C:11]([NH:15][C:16](=[O:28])[C@@H:17]([N:19]([CH3:27])[C:20](=[O:26])[O:21][C:22]([CH3:25])([CH3:24])[CH3:23])[CH3:18])[CH:12]=[CH:13][CH:14]=1)C1C=CC=CC=1>CO.O1CCCC1.[C].[Pd]>[OH:8][C:9]1[CH:10]=[C:11]([NH:15][C:16](=[O:28])[C@@H:17]([N:19]([CH3:27])[C:20](=[O:26])[O:21][C:22]([CH3:23])([CH3:25])[CH3:24])[CH3:18])[CH:12]=[CH:13][CH:14]=1

Participants

5

Reactant 1

HCID 90051744HCID 90051744, compound

Product 1

HCID 90051746HCID 90051746, compoundYield 107%

Reagents, catalysts & solvents 3

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To 10% palladium-carbon (100 mg), a solution of (S)-tert-butyl (1-((3-(benzyloxy)phenyl)amino)-1-oxopropan-2-yl)(methyl)carbamate (E15, 166 mg) in methanol (4 mL) and tetrahydrofuran (2 mL) was added at room temperature, and the mixture was stirred at the same temperature for 5 hours and 30 minutes under a hydrogen atmosphere. The insoluble matter was removed by filtration through Cerite, and then the solvent was evaporated under reduced pressure to obtain (S)-tert-butyl (1-((3-hydroxyphenyl)amino)-1-oxopropan-2-yl)(methyl)carbamate (E16, 136 mg).

Workup

  1. customThe insoluble matter was removed by filtration through Cerite
  2. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-baccf7b5b1a94bff8a22a18d187daf8b
Source dataset
uspto-grants-2015_09
Patent number
US09145415B2

Reaction notes

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