1-(3-Mercapto-1-oxopropyl)-L-proline → 1-[3-[[(ethoxy)carbonyl]thio]propanoyl]-L-proline

HRID 262561Notes

Reaction equation

HRID 262561 reaction equation
C[CH2:2][O:3][CH2:4][CH3:5].ClC([O-])=[O:8].[SH:10][CH2:11][CH2:12][C:13]([N:15]1[CH2:22][CH2:21][CH2:20][C@H:16]1[C:17]([OH:19])=[O:18])=[O:14]>C(=O)(O)[O-].[Na+]>[CH2:4]([O:3][C:2]([S:10][CH2:11][CH2:12][C:13]([N:15]1[CH2:22][CH2:21][CH2:20][C@H:16]1[C:17]([OH:19])=[O:18])=[O:14])=[O:8])[CH3:5]

Participants

4

Reactant 2

HCID 999781-(3-Mercapto-1-oxopropyl)-L-prolineHCID 21319165Ether chloroformate

Product 1

HCID 537685991-[3-[[(ethoxy)carbonyl]thio]propanoyl]-L-proline

Reagents, catalysts & solvents 1

HCID 516892Sodium BicarbonateSolvent

Procedure

Ether chloroformate (1.2 g.) is added to a solution of 3-mercaptopropanoyl-L-proline [2.03 g.) in normal sodium bicarbonate (30 ml.) and the mixture is stirred vigorously at 5° for one hour, and for two hours at room temperature. After acidification with concentrated hydrochloric acid, the mixture is extracted with ethyl acetate. The organic phase is washed with water, dried over magnesium sulfate, and concentrated to dryness to yield 1-[3-[[(ethoxy)carbonyl]thio]propanoyl]-L-proline.

Workup

  1. extractionAfter acidification with concentrated hydrochloric acid, the mixture is extracted with ethyl acetate
  2. washThe organic phase is washed with water
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-1a6654ee32314ac58843c323a8ad00b9
Source dataset
uspto-grants-1979_05
Patent number
US04154840

Reaction notes

Loading…