Ethyl Acetate → HCID 86586124, compound

HRID 751457Notes

Reaction equation

HRID 751457 reaction equation
C(OC([N:11]1[CH2:17][CH2:16][CH2:15][CH:14]([NH:18][C:19](=[O:37])[C@@H:20]([NH:25][C:26]([C:28]2[O:29][C:30]3[CH:36]=[CH:35][CH:34]=[CH:33][C:31]=3[CH:32]=2)=[O:27])[CH2:21][CH:22]([CH3:24])[CH3:23])[CH:13]([OH:38])[CH2:12]1)=O)C1C=CC=CC=1.C(OCC)(=O)C.[H][H]>CO.[Pd]>[OH:38][CH:13]1[CH:14]([NH:18][C:19]([C@@H:20]([NH:25][C:26]([C:28]2[O:29][C:30]3[CH:36]=[CH:35][CH:34]=[CH:33][C:31]=3[CH:32]=2)=[O:27])[CH2:21][CH:22]([CH3:23])[CH3:24])=[O:37])[CH2:15][CH2:16][CH2:17][NH:11][CH2:12]1

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 53783522HCID 53783522, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 86586124HCID 86586124, compoundYield 97.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 4-{(S)-2-[(benzofuran-2-carbonyl)-amino]-4-methyl-pentanoylamino}-3-hydroxy-azepane-1-carboxylic acid benzyl ester of Example 78b (1.6 g) in methanol:ethyl acetate (50 mL: 100 mL) was added 10% Pd/C. The reaction was stirred under a balloon of hydrogen for 2 hours whereupon it was filtered and concentrated to provide the title compound (1.16 g): MS(EI) 387 (M+H+).

Workup

  1. filtrationwas filtered
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-d2e07ed1976646a1900ffa22988c34e0
Source dataset
uspto-grants-2008_07
Patent number
US07405209B2

Reaction notes

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