Water → N-benzenesulfonylglycyl-L-proline

HRID 1073991Notes

Reaction equation

HRID 1073991 reaction equation
C([O:8][C:9](=[O:28])[C@@H:10]1[CH2:14][CH2:13][CH2:12][N:11]1[C:15](=[O:27])[CH2:16][NH:17][S:18]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)(=[O:20])=[O:19])C1C=CC=CC=1.Cl.[Na].O>CO.C(OCC)(=O)C>[C:21]1([S:18]([NH:17][CH2:16][C:15]([N:11]2[CH2:12][CH2:13][CH2:14][C@H:10]2[C:9]([OH:28])=[O:8])=[O:27])(=[O:20])=[O:19])[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

Participants

6

Reactant 3

HCID 962WaterHCID 14858890N-benzenesulfonylglycyl-L-proline benzylesterHCID 23872008Sodium hydrochloride

Product 1

HCID 14858888N-benzenesulfonylglycyl-L-prolineYield 45.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

N-benzenesulfonylglycyl-L-proline benzylester (1.91 g, 4.7 mmole) was dissolved in methanol (6 ml), 1N aqueous sodium hydrochloride (6 ml) was added, and stirred for 3 hours at a temperature between 30° C. and 35° C. Water (20 ml) was added to the solution and the mixture was washed with two 20 ml portions of diethyl ether and then adjusted to pH 1.5 with 1N aqueous hydrochloric acid. The solvent was removed by distillation under reduced pressure and the solid material thus obtained was dispersed in ethyl acetate (50 ml) and the mixture was dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure to give a glassy residue and it was recrystallized from ethyl acetate and petroleum ether to obtain N-benzenesulfonylglycyl-L-proline(yield: 0.67 g, 45.2%).

Workup

  1. washthe mixture was washed with two 20 ml portions of diethyl ether
  2. customThe solvent was removed by distillation under reduced pressure
  3. customthe solid material thus obtained
  4. dry with materialthe mixture was dried over anhydrous magnesium sulfate
  5. distillationThe solvent was distilled off under reduced pressure
  6. customto give a glassy residue and it
  7. customwas recrystallized from ethyl acetate and petroleum ether

Sources & evidence

ORD record
ord-65fe8363c34144bd8ae064de236489bd
Source dataset
uspto-grants-1990_11
Patent number
US04971993

Reaction notes

Loading…