Methanesulfonyl chloride → HCID 86608971, compound

HRID 1715318Notes

Reaction equation

HRID 1715318 reaction equation
[CH:1]([NH:5][C:6](=[O:26])[CH:7]([O:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]#[N:21])=[C:16]([C:22]([F:25])([F:24])[F:23])[CH:15]=1)[C:8]([CH3:12])([CH3:11])[CH2:9][OH:10])([CH2:3][CH3:4])[CH3:2].[CH3:27][S:28](Cl)(=[O:30])=[O:29]>N1C=CC=CC=1.ClCCl>[CH:1]([NH:5][C:6]([CH:7]([O:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]#[N:21])=[C:16]([C:22]([F:24])([F:25])[F:23])[CH:15]=1)[C:8]([CH3:11])([CH3:12])[CH2:9][O:10][S:28]([CH3:27])(=[O:30])=[O:29])=[O:26])([CH2:3][CH3:4])[CH3:2]

Participants

5

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 68508938HCID 68508938, compound

Product 1

HCID 86608971HCID 86608971, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

To a stirring solution comprised of two(2) N-sec-butyl-2-(4-cyano-3-trifluoromethyl-phenoxy)-4-hydroxy-3,3-dimethyl-butyramide diastereomers (1.63 g; 4.38 mmol) in pyridine (10 mL) at 0° C. under a nitrogen atmosphere is added methanesulfonyl chloride (0.75 g; 6.5 mmol). The reaction mixture is stirred cold for 3.5 hours. The reaction mixture is diluted with dichloromethane and is washed with 1N aqueous hydrochloric acid and with brine. The organic phase is dried over anhydrous magnesium sulfate and is concentrated in vacuo (the water bath temperature is not raised above 23° C.) to afford 1.892 g of a foam; HPLC UV purity: 99.3% (two diastereomers.)

Workup

  1. washis washed with 1N aqueous hydrochloric acid and with brine
  2. dry with materialThe organic phase is dried over anhydrous magnesium sulfate
  3. concentrationis concentrated in vacuo (the water bath temperature
  4. temperatureis not raised above 23° C.)

Sources & evidence

ORD record
ord-8b035878d5df4561a87aec143b52805a
Source dataset
uspto-grants-2010_09
Patent number
US07799823B2

Reaction notes

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