Ammonia → HCID 12878442, compound

HRID 444506Notes

Reaction equation

HRID 444506 reaction equation
C([S:9][CH2:10][C@@H:11]([CH3:28])[C:12]([N:14]1[CH:18]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:17][CH2:16][CH:15]1[C:25]([OH:27])=[O:26])=[O:13])(=O)C1C=CC=CC=1.N>CO>[SH:9][CH2:10][C@@H:11]([CH3:28])[C:12]([N:14]1[CH:18]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:17][CH2:16][CH:15]1[C:25]([OH:27])=[O:26])=[O:13]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 12878437HCID 12878437, compound

Product 1

HCID 12878442HCID 12878442, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

20 g of 1-[(2S)-S-benzoyl-3-mercapto-2-methylpropanoyl]-5-phenyl-2-pyrrolidinecarboxylic acid is dissolved in 50 ml of methanol. To this solution 100 ml of conc. ammonia is added, and the mixture is stirred at room temperature for 1.5 hours. Excess ammonia and methanol are removed in vacuo, and the residue is washed with ethyl acetate. The aqueous layer is acidified with conc. hydrochloric acid, and extracted with ethyl acetate. The organic layer is washed with saturated sodium chloride solution, dried over magnesium sulfate, and concentrated in vacuo to give the titled compound, yield 8.5 g (58%), mp. 138.0°-142.5° C. (ethyl acetate), [α]D29 -29.4° (c=1.0, methanol).

Workup

  1. customExcess ammonia and methanol are removed in vacuo
  2. washthe residue is washed with ethyl acetate
  3. extractionextracted with ethyl acetate
  4. washThe organic layer is washed with saturated sodium chloride solution
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-de37fd3be43a418ca04c993c6158cf8b
Source dataset
uspto-grants-1981_04
Patent number
US04264620

Reaction notes

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