(2S)-2-[(1R,2S)-2-benzyloxycarbonyl-1-methylsulfanyl-propyl]-pyrrolidine-1-carboxylic acid tert-butyl ester → (2S)-2-[(R,2S)-2-carboxy-1-methylsulfanyl-propyl]-pyrrolidine-1-carboxylic acid tert-butyl ester

HRID 1582734Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1582734
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH2:10][C@H:9]1[C@H:13]([S:26][CH3:27])[C@H:14]([C:16]([O:18]CC1C=CC=CC=1)=[O:17])[CH3:15])=[O:7])([CH3:4])([CH3:3])[CH3:2]>CCO.[OH-].[OH-].[Pd+2]>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH2:10][C@H:9]1[C@H:13]([S:26][CH3:27])[C@H:14]([C:16]([OH:18])=[O:17])[CH3:15])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Komponenten

4

Edukt 1

HCID 58660116(2S)-2-[(1R,2S)-2-benzyloxycarbonyl-1-methylsulfanyl-propyl]-pyrrolidine-1-carboxylic acid tert-butyl ester

Produkt 1

HCID 11522334(2S)-2-[(R,2S)-2-carboxy-1-methylsulfanyl-propyl]-pyrrolidine-1-carboxylic acid tert-butyl esterAusbeute 99,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 9942167Palladium hydroxideKatalysatorHCID 702EthanolLösungsmittel

Versuchsvorschrift

A mixture of (2S)-2-[(1R,2S)-2-benzyloxycarbonyl-1-methylsulfanyl-propyl]-pyrrolidine-1-carboxylic acid tert-butyl ester (4.4 g, 11.2 mmol) and Pd(OH)2 on carbon(ca.20 wt %, 2.0 g) in EtOH (50 mL) was stirred at room temperature under H2 atmosphere. After being stirred at room temperature for 14 hr, the mixture was filtrated through a pad of celite and washed with MeOH. The filtrate and washings were combined and concentrated in vacuo to give a crude gum, which was purified by flush column chromatography (hexane:AcOEt=1:1) to give (2S)-2-[(R,2S)-2-carboxy-1-methylsulfanyl-propyl]-pyrrolidine-1-carboxylic acid tert-butyl ester as a gum (3.39 g, 98%).

Aufarbeitung

  1. stirringAfter being stirred at room temperature for 14 hr
  2. filtrationthe mixture was filtrated through a pad of celite
  3. washwashed with MeOH
  4. concentrationconcentrated in vacuo
  5. customto give a crude gum, which
  6. customwas purified
  7. customby flush column chromatography (hexane:AcOEt=1:1)

Quellen und Nachweise

ORD-Eintrag
ord-574e81d9380c4d1d9c0c61225ac8f6be
Quelldatensatz
uspto-grants-2004_05
Patentnummer
US06737409B2

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