Pyridine → N-[4-cyano-3-trifluoromethyl-phenyl]-2-hydroxy-3-methanesulfonyloxy-2-methyl-propionamide

HRID 1269468

Reaction equation

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

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of 46 g (0.16 mol) of N-[4-cyano-3-trifluoromethyl-phenyl]-2,3-dihydroxy-2-methyl-propionamide in 1 1 of dichloromethane and 46 ml (0.57 mol) of dry pyridine was cooled to 0° C. and 46 ml (0.59 mol) of methanesulfonyl chloride was added dropwise. The mixture was stirred at 0° C. for 5 h, then washed three times with 500 ml of saturated aqueous sodium hydrogen carbonate, 500 ml of 10% aqueous hydrochloric acid and 500 ml of brine. The organic layer was dried over sodium sulfate and concentrated in vacuum. The residue was crystallized with 200 ml of petroleum ether, which has a boiling range of 40–70° C.

Workup

washwashed three times with 500 ml of saturated aqueous sodium hydrogen carbonate, 500 ml of 10% aqueous hydrochloric acid and 500 ml of brine
dry with materialThe organic layer was dried over sodium sulfate
concentrationconcentrated in vacuum
customThe residue was crystallized with 200 ml of petroleum ether, which

Sources & evidence

ORD record: ord-b35866d175fd4d758effefbba81c681b
Source dataset: uspto-grants-2007_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07199257B1

Linked notes

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