Ethyl isocyanate → 1-[3-[[(ethylamino)carbonyl]thio]propanoyl]-L-proline

HRID 262564Notes

Reaction equation

HRID 262564 reaction equation
[CH2:1]([N:3]=[C:4]=[O:5])[CH3:2].[SH:6][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+]>N1C=CC=CC=1>[CH2:1]([NH:3][C:4]([S:6][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])=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 8022Ethyl isocyanateHCID 14798Sodium HydroxideHCID 999781-(3-Mercapto-1-oxopropyl)-L-proline

Product 1

HCID 542925261-[3-[[(ethylamino)carbonyl]thio]propanoyl]-L-proline

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Ethylisocyanate (0.45 ml) is added to a solution of 1-(3-mercaptopropanoyl)-L-proline (1 g) in a mixture of N sodium hydroxide (5 ml) and pyridine (5 ml). The solution is heated at 40° for four hours and concentrated in vacuo. The residue is distributed between 0.1 N hydrochloric acid and ethyl acetate. The organic layer is washed with water, dried over magnesium sulfate and concentrated to dryness to yield 1-[3-[[(ethylamino)carbonyl]thio]propanoyl]-L-proline. The dicyclohexylammonium salt is prepared by adding dicyclohexylamine to a solution of the free acid in ethyl acetate, m.p. 150°-152°.

Workup

  1. temperatureThe solution is heated at 40° for four hours
  2. concentrationconcentrated in vacuo
  3. washThe organic layer is washed with water
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-430674e711934d368270d009c446e400
Source dataset
uspto-grants-1979_05
Patent number
US04154840

Reaction notes

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