(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 881896Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 881896
[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]

Komponenten

3

Edukt 1

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-69355fd570df486b867dbfaa677e538c
Quelldatensatz
uspto-grants-2015_03
Patentnummer
US08993631B2

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