(E)-(R)-4-tert-butoxycarbonylamino-5-(3'-chloro-biphenyl-4-yl)-2-methyl-pent-2-enoic acid ethyl ester → (S)-4-tert-butoxycarbonylamino-5-(3'-chloro-biphenyl-4-yl)-2-methyl-pentanoic acid ethyl ester

HRID 881896Notes

Reaction equation

HRID 881896 reaction equation
[CH2:1]([O:3][C:4](=[O:31])/[C:5](/[CH3:30])=[CH:6]/[C@H:7]([NH:22][C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([Cl:21])[CH:16]=2)=[CH:11][CH:10]=1)[CH3:2]>C(O)C>[CH2:1]([O:3][C:4](=[O:31])[C@@H:5]([CH3:30])[CH2:6][CH:7]([NH:22][C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([Cl:21])[CH:16]=2)=[CH:11][CH:10]=1)[CH3:2]

Participants

3

Reactant 1

HCID 59608250(E)-(R)-4-tert-butoxycarbonylamino-5-(3'-chloro-biphenyl-4-yl)-2-methyl-pent-2-enoic acid ethyl ester

Product 1

HCID 67505776(S)-4-tert-butoxycarbonylamino-5-(3'-chloro-biphenyl-4-yl)-2-methyl-pentanoic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Next, to a solution of (E)-(R)-4-tert-butoxycarbonylamino-5-(3′-chloro-biphenyl-4-yl)-2-methyl-pent-2-enoic acid ethyl ester (2.5 g, 5.63 mmol) in ethanol (20 mL) is added PUC (250 mg) and the mixture is stirred overnight under an atmosphere of hydrogen (H2 balloon). The catalyst is filtered through a Celite pad and, the filtrate is concentrated to give (S)-4-tert-butoxycarbonylamino-5-(3′-chloro-biphenyl-4-yl)-2-methyl-pentanoic acid ethyl ester.

Workup

  1. filtrationThe catalyst is filtered through a Celite pad
  2. concentrationthe filtrate is concentrated

Sources & evidence

ORD record
ord-69355fd570df486b867dbfaa677e538c
Source dataset
uspto-grants-2015_03
Patent number
US08993631B2

Reaction notes

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