Ethyl chloroformate → 1-[3-[[(ethoxy)carbonyl]thio]propanoyl]-L-proline

HRID 2419429Notes

Reaction equation

HRID 2419429 reaction equation
Cl[C:2]([O:4][CH2:5][CH3:6])=[O:3].[SH:7][CH2:8][CH2:9][C:10]([N:12]1[CH2:19][CH2:18][CH2:17][C@H:13]1[C:14]([OH:16])=[O:15])=[O:11]>C(=O)(O)[O-].[Na+]>[CH2:5]([O:4][C:2]([S:7][CH2:8][CH2:9][C:10]([N:12]1[CH2:19][CH2:18][CH2:17][C@H:13]1[C:14]([OH:16])=[O:15])=[O:11])=[O:3])[CH3:6]

Participants

4

Reactant 2

HCID 10928Ethyl chloroformateHCID 999781-(3-Mercapto-1-oxopropyl)-L-proline

Product 1

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

Reagents, catalysts & solvents 1

HCID 516892Sodium BicarbonateSolvent

Procedure

Ethyl 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. waitfor two hours at room temperature
  2. extractionAfter acidification with concentrated hydrochloric acid, the mixture is extracted with ethyl acetate
  3. washThe organic phase is washed with water
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-f70559b38f554c36b75b2e42e2dd3825
Source dataset
uspto-grants-1978_08
Patent number
US04105776

Reaction notes

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