(S)-2-[(azepane-1-carbonyl)-amino]-4-methyl-pentanoic acid benzyl ester → (2S)-2-(azepane-1-carbonylamino)-4-methylpentanoic acid

HRID 1757295Notes

Reaction equation

HRID 1757295 reaction equation
C([O:8][C:9](=[O:25])[C@H:10]([CH2:21][CH:22]([CH3:24])[CH3:23])[NH:11][C:12]([N:14]1[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1)=[O:13])C1C=CC=CC=1.[H][H]>CO.[Pd]>[N:14]1([C:12]([NH:11][C@H:10]([C:9]([OH:25])=[O:8])[CH2:21][CH:22]([CH3:24])[CH3:23])=[O:13])[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1

Participants

5

Reactant 2

HCID 10593708(S)-2-[(azepane-1-carbonyl)-amino]-4-methyl-pentanoic acid benzyl esterHCID 178418361HCID 178418361, compound

Product 1

HCID 7530182(2S)-2-(azepane-1-carbonylamino)-4-methylpentanoic acidYield 92.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

The compound obtained in (1) (1.75 g) was dissolved in methanol (30 ml). 10% Pd-C (0.30 g) was added and the mixture was stirred vigorously at room temperature under atmospheric pressure of hydrogen for 1.5 h. The catalyst was filtered off and the filtrate was concentrated to give the product (1.2 g) as a colorless foam.

Workup

  1. filtrationThe catalyst was filtered off
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-e3d2b0a8d53849a69192d6fd7a896e99
Source dataset
uspto-grants-1995_08
Patent number
US05444152

Reaction notes

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