1-Propanesulfonyl chloride → Propane-1-sulfonic acid 2-[cyclopropyl-(propane-1-sulfonyl)-amino]ethyl ester

HRID 2177122Notes

Reaction equation

HRID 2177122 reaction equation
[CH:1]1([N:4]([CH2:11][CH2:12][OH:13])[S:5]([CH2:8][CH2:9][CH3:10])(=[O:7])=[O:6])[CH2:3][CH2:2]1.[CH2:14]([S:17](Cl)(=[O:19])=[O:18])[CH2:15][CH3:16]>C(Cl)Cl.CN(C1C=CN=CC=1)C>[CH:1]1([N:4]([S:5]([CH2:8][CH2:9][CH3:10])(=[O:7])=[O:6])[CH2:11][CH2:12][O:13][S:17]([CH2:14][CH2:15][CH3:16])(=[O:19])=[O:18])[CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 662791-Propanesulfonyl chlorideHCID 43577530Propane-1-sulfonic acid cyclopropyl-(2-hydroxy-ethyl)-amide

Product 1

HCID 59547799Propane-1-sulfonic acid 2-[cyclopropyl-(propane-1-sulfonyl)-amino]ethyl esterYield 78.8%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent3×

Procedure

To a solution of propane-1-sulfonic acid cyclopropyl-(2-hydroxy-ethyl)-amide (150 mg, 0.8 mmol) in CH2Cl2 and DMAP (97 mg, 0.8 mmol) was added dropwise a solution of propane-1-sulfonyl chloride (97 mg, 0.8 mmol) in CH2Cl2. The resulting mixture was stirred at room temperature over night, diluted with 50 ml of CH2Cl2, extracted subsequently with water, 1 M HCl, and brine, tried over Na2SO4, filtered and the solvent evaporated to obtain 197.5 mg of product which was used in the next step without further purification.

Workup

  1. extractionextracted subsequently with water, 1 M HCl, and brine
  2. filtrationfiltered
  3. customthe solvent evaporated

Sources & evidence

ORD record
ord-18955bef3b1d408982b466a6ba10e914
Source dataset
uspto-grants-2015_06
Patent number
US09067871B2

Reaction notes

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