p-Bromobenzenesulfonyl chloride → N-[4-cyano-3-trifluoromethyl-phenyl]-2-hydroxy-3-[4-bromophenyl-sulfonyloxy]-2-methyl-propionamide

HRID 1269470Notes

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].[Br:21][C:22]1[CH:27]=[CH:26][C:25]([S:28](Cl)(=[O:30])=[O:29])=[CH:24][CH:23]=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:28]([C:25]2[CH:26]=[CH:27][C:22]([Br:21])=[CH:23][CH:24]=2)(=[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 5 g (17.35 mmol) 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 8.86 g (34.70 mmol) of 4-bromo-benzenesulfonyl 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 hydrogencarbonate, 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 hydrogencarbonate
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-d3fdf4c1a68a4858b4fc24a3127d4569
Source dataset: uspto-grants-2007_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07199257B1

Reaction notes

Loading…