Benzenesulfonyl chloride → HCID 14858872, compound

HRID 1074011Notes

Reaction equation

HRID 1074011 reaction equation
Cl.[CH2:2]([O:9][C:10](=[O:22])[C@@H:11]1[CH2:15][CH2:14][CH2:13][N:12]1[C:16](=[O:21])[C@H:17]([CH2:19][OH:20])[NH2:18])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C(N(CC)CC)C.[C:30]1([S:36](Cl)(=[O:38])=[O:37])[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>C(Cl)Cl>[CH2:2]([O:9][C:10](=[O:22])[C@@H:11]1[CH2:15][CH2:14][CH2:13][N:12]1[C:16](=[O:21])[C@H:17]([CH2:19][OH:20])[NH:18][S:36]([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)(=[O:38])=[O:37])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 7369Benzenesulfonyl chlorideHCID 8471TriethylamineHCID 14858903HCID 14858903, compound

Product 1

HCID 14858872HCID 14858872, compoundYield 90.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

L-seryl-L-proline benzylester hydrochloride (1.64 g, 5 mmole) was dissolved in methylene chloride (30 ml), and triethylamine (1.11 g, 11 mmole) was added thereto at -30° C. Methylene chloride (10 ml) solution of benzene sulfonyl chloride (0.86 g, 5 mmole) was added dropwise thereto. 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 thereto. The mixture 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 off under reduced pressure to obtain N-benzenesulfonyl-L-seryl-L-proline benzylester (yield: 1.96 g, 90.6%).

Workup

  1. customat -30° C
  2. waitfor 5 hours at room temperature
  3. washThe mixture was washed with 5% aqueous sodium bicarbonate (100 ml
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-95b42ba418834c9784eca65b5630c66d
Source dataset
uspto-grants-1990_11
Patent number
US04971993

Reaction notes

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