Water → HCID 21967948, compound

HRID 1003957Notes

Reaction equation

HRID 1003957 reaction equation
C[O:2][C:3](=[O:30])[C@@H:4]([NH:14][C:15](=[O:29])[CH:16]([CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[CH2:17][S:18]C(=O)C)[CH2:5][S:6]SC[C@H](N)C(O)=O.O.O.O.O.O.O.O.O.O.[S-2].[Na+].[Na+].SC[C@H]([C@@H](CS)O)O.O>CO>[CH2:22]([CH:16]([CH2:17][SH:18])[C:15]([NH:14][C@H:4]([C:3]([OH:30])=[O:2])[CH2:5][SH:6])=[O:29])[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Participants

6

Reactant 4

HCID 962WaterHCID 73972Sodium sulfide nonahydrateHCID 446094D-1,4-DithiothreitolHCID 86755298HCID 86755298, compound

Product 1

HCID 21967948HCID 21967948, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

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.

Workup

  1. extractionextracted with chloroform (2×20 ml)
  2. customdried
  3. filtration(MgSO4) filtered
  4. customevaporated to a clear oil
  5. additionthe title compound as an approximately equimolar mixture of diastereoisomers

Sources & evidence

ORD record
ord-f71826c23b6947038f292ffcb03c6519
Source dataset
uspto-grants-2000_04
Patent number
US06048852

Reaction notes

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