Methanesulfonyl chloride → HCID 54400977, compound

HRID 266285Notes

Reaction equation

HRID 266285 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[Cl:6][C:7]1[CH:12]=[CH:11][C:10]([S:13]([NH:16][C@@H:17]([CH2:32][OH:33])[C:18]([NH:20][C:21]2[CH:26]=[CH:25][C:24]([C:27]([O:29][CH2:30][CH3:31])=[O:28])=[CH:23][CH:22]=2)=[O:19])(=[O:15])=[O:14])=[CH:9][CH:8]=1>N1C=CC=CC=1>[Cl:6][C:7]1[CH:8]=[CH:9][C:10]([S:13]([NH:16][C@@H:17]([CH2:32][O:33][S:2]([CH3:1])(=[O:4])=[O:3])[C:18]([NH:20][C:21]2[CH:26]=[CH:25][C:24]([C:27]([O:29][CH2:30][CH3:31])=[O:28])=[CH:23][CH:22]=2)=[O:19])(=[O:14])=[O:15])=[CH:11][CH:12]=1

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chloride2×HCID 53906075HCID 53906075, compound

Product 1

HCID 54400977HCID 54400977, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Methanesulfonyl chloride (hereinafter referred to as mesyl chloride) (96 μl) was added to a solution of (S)-2-(4-chlorobenzenesulfonylamino)-N-(4-ethoxycarbonylphenyl)-3-hydroxypropanamide (132 mg) in pyridine (2.5 ml) and the mixture was stirred for 2 hours at room temperature. The reaction mixture was poured into a saturated saline solution and extracted with ethyl acetate. The combined ethyl acetate layers were washed with saturated saline solution, 1N HCl, and a saturated saline solution, and dried over Na2SO4. Then, the solvent was evaporated under reduced pressure to obtain (S)-2-(4-chlorobenzenesulfonylamino)-N-(4-ethoxycarbonylphenyl)-3-methanesulfonyloxypropanamide (133 mg).

Workup

  1. additionThe reaction mixture was poured into a saturated saline solution
  2. extractionextracted with ethyl acetate
  3. washThe combined ethyl acetate layers were washed with saturated saline solution, 1N HCl
  4. dry with materiala saturated saline solution, and dried over Na2SO4
  5. customThen, the solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-589c2e7eb9594db1baccf8c80e0dcaf7
Source dataset
uspto-grants-1997_07
Patent number
US05650428

Reaction notes

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