Sodium Hydroxide → HCID 15580536, compound

HRID 1981228Notes

Reaction equation

HRID 1981228 reaction equation
C([S:9][C@@H:10]([CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:11]([NH:13][C@H:14]([C:19]([OH:21])=[O:20])[CH2:15][CH:16]([CH3:18])[CH3:17])=[O:12])(=O)C1C=CC=CC=1.[OH-].[Na+]>CO>[SH:9][C@@H:10]([CH2:22][C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1)[C:11]([NH:13][C@H:14]([C:19]([OH:21])=[O:20])[CH2:15][CH:16]([CH3:18])[CH3:17])=[O:12]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 15580534HCID 15580534, compound

Product 1

HCID 15580536HCID 15580536, compoundYield 98.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2 g N-[(S)-2-benzoylthio-3-phenyl-propionyl]-L-leucine dissolved in 10 ml MeOH are stirred at 0° C. for 1 hour with 10 ml 1N NaOH, and then for 4 hours at 25° C. under a nitrogen atmosphere. The methanol is evaporated off, the material is taken up into water and made acidic to pH 1 with 1N HCl. The resulting gummy precipitate is extracted with ethyl acetate. The organic phase is dried, and evaporated in vacuo, to give 1.45 g N-[(S)-2-mercapto-3-phenyl-propionyl]-L-leucine which crystallizes slowly. M.P.=67°-71° C.

Workup

  1. customThe methanol is evaporated off
  2. extractionThe resulting gummy precipitate is extracted with ethyl acetate
  3. customThe organic phase is dried
  4. customevaporated in vacuo

Sources & evidence

ORD record
ord-738bbadd03d141548b18c2547708e0bd
Source dataset
uspto-grants-1985_04
Patent number
US04513009

Reaction notes

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