Reaktion #1091139

ord-f71826c23b6947038f292ffcb03c6519

Reaktionsgleichung

O
water
O.O.O.O.O.O.O.O.O.[Na+].[Na+].[S-2]
sodium sulfide nonahydrate
O[C@H](CS)[C@H](O)CS
dithiothreitol
COC(=O)[C@H](CSSC[C@H](N)C(=O)O)NC(=O)C(CSC(C)=O)Cc1ccccc1
N-(S-Acetyl-2'-benzyl-3'-mercaptopropionyl)cystine methyl ester
→
O=C(N[C@@H](CS)C(=O)O)C(CS)Cc1ccccc1
N-[2'-Benzyl-3'-mercaptopropionyl]cysteine
Ausbeute 86.0%

Edukte

O
water
O.O.O.O.O.O.O.O.O.[Na+].[Na+].[S-2]
sodium sulfide nonahydrate
O[C@H](CS)[C@H](O)CS
dithiothreitol
COC(=O)[C@H](CSSC[C@H](N)C(=O)O)NC(=O)C(CSC(C)=O)Cc1ccccc1
N-(S-Acetyl-2'-benzyl-3'-mercaptopropionyl)cystine methyl ester

Reagenzien

Keine

Lösungsmittel

CO
methanol

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Extraktionextracted with chloroform (2×20 ml)
  2. 2
    Sonstigedried
  3. 3
    Filtration(MgSO4) filtered
  4. 4
    Sonstigeevaporated to a clear oil
  5. 5
    workup.ADDITIONthe title compound as an approximately equimolar mixture of diastereoisomers

Vorschrift

N-(S-Acetyl-2'-benzyl-3'-mercaptopropionyl)cystine methyl ester (50 mg) was dissolved in degassed methanol (5 ml) and treated with sodium sulfide nonahydrate (300 mg) and dithiothreitol (122 mg). The mixture was stirred at RT for 14 hours then poured into water (30 ml) and extracted with chloroform (2×20 ml), the aqueous phase acidified to pH 1-2 and re-extraced with ethyl acetate (3×10 ml), dried, (MgSO4) filtered and evaporated to a clear oil, the title compound as an approximately equimolar mixture of diastereoisomers, in 86% yield.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US06048852uspto-grants-2000_04