Benzenesulfonyl chloride → N-benzenesulfonylglycyl-L-proline benzylester

HRID 1073990

Reaction equation

HRID 1073990 reaction equation
Cl.[CH2:2]([O:9][C:10](=[O:20])[C@@H:11]1[CH2:15][CH2:14][CH2:13][N:12]1[C:16](=[O:19])[CH2:17][NH2:18])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C(N(CC)CC)C.[C:28]1([S:34](Cl)(=[O:36])=[O:35])[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>C(Cl)Cl>[CH2:2]([O:9][C:10](=[O:20])[C@@H:11]1[CH2:15][CH2:14][CH2:13][N:12]1[C:16](=[O:19])[CH2:17][NH:18][S:34]([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)(=[O:36])=[O:35])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 7369Benzenesulfonyl chlorideHCID 8471TriethylamineHCID 13068147glycyl-L-proline benzylester hydrochloride

Product 1

HCID 14858890N-benzenesulfonylglycyl-L-proline benzylesterYield 94.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

Glycyl-L-proline benzylester hydrochloride (1.49 g, 5 mmole) was dissolved in methylene chloride (30 ml), and triethylamine (1.11 g, 11 mmole) was added thereto at -30° C., and then methylene chloride (10 ml) solution of benzenesulfonylchloride (0.86 g, 5 mmole) was added dropwise. The mixture was stirred for 1 hour at less than 0° C, and then for 5 hours at room temperature, and methylene chloride (60 ml) was added. The mixture thus obtained was washed with 5% aqueous sodium bicarbonate (100 ml, twice), 1N aqueous hydrochloric acid (100 ml, twice) and water (100 ml) in the order given, and dried over anhydrous magnesium sulfate. The solvent was distilled under reduced pressure to give N-benzenesulfonylglycyl-L-proline benzylester (yield: 1.91 g, 94.9%).

Workup

  1. waitfor 5 hours at room temperature
  2. customThe mixture thus obtained
  3. washwas washed with 5% aqueous sodium bicarbonate (100 ml
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationThe solvent was distilled under reduced pressure

Sources & evidence

ORD record
ord-958a0c1fa24948f081e45962559c8a3e
Source dataset
uspto-grants-1990_11
Patent number
US04971993

Linked notes

Loading…