Sodium Hydroxide → HCID 54438664, compound

HRID 262571Notes

Reaction equation

HRID 262571 reaction equation
[CH2:1]([S:3]([O-])=[S:4])[CH3:2].S[CH2:7][CH2:8][C:9]([N:11]1[CH2:18][CH2:17][CH2:16][C@H:12]1[C:13]([OH:15])=[O:14])=[O:10].[OH-].[Na+]>C(O)C.O>[CH2:1]([S:3][S:4][CH2:7][CH2:8][C:9]([N:11]1[CH2:18][CH2:17][CH2:16][C@H:12]1[C:13]([OH:15])=[O:14])=[O:10])[CH3:2]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 999781-(3-Mercapto-1-oxopropyl)-L-prolineHCID 20578574HCID 20578574, compound

Product 1

HCID 54438664HCID 54438664, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A solution of ethylthiosulfinate (8.4 g) in ethanol (50 ml) is added to an aqueous solution of 3-mercaptopropanoyl-L-proline (10 g) maintained at pH 6-7 by careful addition of sodium hydroxide. The mixture is stirred vigorously at room temperature until negative thiol reaction. The mixture is diluted with water, adjusted to pH 8 and extracted with ethyl acetate, the aqueous phase is acidified to pH 3 and extracted again with ethyl acetate. This latter extract is washed with water, dried and concentrated to dryness to yield 1-[3-(ethyldithio)propanoyl]-L-proline.

Workup

  1. extractionextracted with ethyl acetate
  2. extractionextracted again with ethyl acetate
  3. extractionThis latter extract
  4. washis washed with water
  5. customdried
  6. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-2a5ee0aaebc042b9b7d7ac1c8eeae55e
Source dataset
uspto-grants-1979_05
Patent number
US04154840

Reaction notes

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