4-Toluenesulfonyl chloride → N-[4-cyano-3-trifluoromethyl-phenyl]-2-hydroxy-3-[4-methylphenyl-sulfonyloxy]-2-methyl-propionamide

HRID 1269469Notes

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].[C:21]1([CH3:31])[CH:26]=[CH:25][C:24]([S:27](Cl)(=[O:29])=[O:28])=[CH:23][CH:22]=1>N1C=CC=CC=1.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:27]([C:24]2[CH:25]=[CH:26][C:21]([CH3:31])=[CH:22][CH:23]=2)(=[O:29])=[O:28])=[CH:5][C:4]=1[C:17]([F:19])([F:18])[F:20])#[N:2]

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of 5 g (17.35 mol) of N-[4-cyano-3-trifluoromethyl-phenyl]-2,3-dihydroxy-2-methyl-propionamide in 50 ml of dry pyridine was cooled to 0° C. and 10 g (52.45 mmol) of p-toluenesulfonyl chloride was added in small portions. The mixture was stirred at 0° C. for 5 h, then diluted with 200 ml of dichloromethane, washed three times with 50 ml of saturated aqueous sodium hydrogen carbonate, twice with 50 ml of 10% aqueous hydrochloric acid and 50 ml of brine. The organic layer was dried over sodium sulfate and concentrated in vacuum. The residue was crystallized from a 1:5 mixture of ethyl acetate/petroleum ether, which has a boiling range of 40–70° C.

Workup

washwashed three times with 50 ml of saturated aqueous sodium hydrogen carbonate
dry with materialThe organic layer was dried over sodium sulfate
concentrationconcentrated in vacuum
customThe residue was crystallized from a 1:5 mixture of ethyl acetate/petroleum ether, which

Sources & evidence

ORD record: ord-bebd325dfe5346c8b105fe26dc350bdc
Source dataset: uspto-grants-2007_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07199257B1

Reaction notes

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