Ammonia → HCID 14181430, compound

HRID 1252805Notes

Reaction equation

HRID 1252805 reaction equation
C([S:4][CH2:5][CH2:6][S:7]([N:10]1[CH2:17][CH2:16][CH2:15][C@H:11]1[C:12]([OH:14])=[O:13])(=[O:9])=[O:8])(=O)C.N.Cl>O>[SH:4][CH2:5][CH2:6][S:7]([N:10]1[CH2:17][CH2:16][CH2:15][C@H:11]1[C:12]([OH:14])=[O:13])(=[O:8])=[O:9]

Participants

5

Reactant 3

HCID 222AmmoniaHCID 313Hydrochloric AcidHCID 14181428HCID 14181428, compound

Product 1

HCID 14181430HCID 14181430, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

N-[[2-(Acetylthio)ethyl]sulfonyl]-L-proline (640 mg, 0.0023 mole) is dissolved in 5 ml of water and 5 mg of concentrated ammonia and stirred 1 hour under nitrogen. The solution is acidified with concentrated hydrochloric acid, extracted with ethyl acetate, and the extracts are washed with brine, dried (MgSO4) and evaporated to an oily residue which is applied to a 75 ml silica gel column. Elution with 10% acetic acid/benzene affords a main fraction which is crystallized from chloroform/hexane, to obtain 440 mg (81%) of 1-[(2-mercaptoethyl)sulfonyl]-L-proline, m.p. 99°-101°.

Workup

  1. extractionextracted with ethyl acetate
  2. washthe extracts are washed with brine
  3. dry with materialdried (MgSO4)
  4. customevaporated to an oily residue which
  5. washElution with 10% acetic acid/benzene
  6. customaffords a main fraction which
  7. customis crystallized from chloroform/hexane

Sources & evidence

ORD record
ord-67859a6ce4774050ae1456f47d211bf8
Source dataset
uspto-grants-1988_05
Patent number
US04745124

Reaction notes

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