Ammonia → HCID 44317202, compound

HRID 2413363Notes

Reaction equation

HRID 2413363 reaction equation
N.C([S:5][CH:6]1[CH2:10][CH2:9][CH2:8][CH:7]1[C:11]([N:13]1[CH2:20][CH2:19][CH2:18][C@H:14]1[C:15]([OH:17])=[O:16])=[O:12])(=O)C>CO>[SH:5][CH:6]1[CH2:10][CH2:9][CH2:8][CH:7]1[C:11]([N:13]1[CH2:20][CH2:19][CH2:18][C@H:14]1[C:15]([OH:17])=[O:16])=[O:12]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 54025763HCID 54025763, compound

Product 1

HCID 44317202HCID 44317202, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Conditions

Temperature
0 °C

Procedure

A mixture of 100 ml of anhydrous methanol and 100 ml of ammonia saturated anhydrous methanol, is added dropwise to a solution of 24.5 g (0.086 mole) of 1-[(2-acetylthiocyclopentyl)carbonyl]-L-proline in 50 ml of methanol cooled to 0° C. and maintained with stirring under nitrogen atmosphere. Once the addition is terminated the reaction mixture is stirred at room temperature under nitrogen for further four hours, then the solvent is evaporated and the residue is purified by column chromatography on Dowex 50® (a polystirene sulfonated resin) eluting with distilled water. Yield: 18.5 g (88%) of 1-[(2-mercaptocyclopentyl)carbonyl]-L-proline with the following characteristics: [α]D25 =-139.3° (C=1% in CHCl3).

Workup

  1. temperaturemaintained
  2. additionOnce the addition
  3. customis terminated the reaction mixture
  4. stirringis stirred at room temperature under nitrogen for further four hours
  5. customthe solvent is evaporated
  6. customthe residue is purified by column chromatography on Dowex 50® (a polystirene sulfonated resin)
  7. washeluting with distilled water
  8. custom[α]D25 =-139.3° (C=1% in CHCl3)

Sources & evidence

ORD record
ord-96a1b69d133d47f9b29c21b00217412d
Source dataset
uspto-grants-1985_01
Patent number
US04496743

Reaction notes

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