Methanol → 3-[4-Methoxy-3-[N-(4-trifluoromethylbenzyl)]carbamoylphenyl]-2-(methylsulfonyl)propionic acid

HRID 49536Notes

Reaction equation

CO.[CH3:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][CH:12]([S:17]([CH3:20])(=[O:19])=[O:18])[C:13]([O:15]C)=[O:14])=[CH:7][C:6]=1[C:21](=[O:34])[NH:22][CH2:23][C:24]1[CH:29]=[CH:28][C:27]([C:30]([F:33])([F:32])[F:31])=[CH:26][CH:25]=1.[OH-].[Na+]>O>[CH3:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][CH:12]([S:17]([CH3:20])(=[O:18])=[O:19])[C:13]([OH:15])=[O:14])=[CH:7][C:6]=1[C:21](=[O:34])[NH:22][CH2:23][C:24]1[CH:25]=[CH:26][C:27]([C:30]([F:31])([F:33])[F:32])=[CH:28][CH:29]=1

Participants

Conditions

Temperature: 50 °C

Procedure

Into 6 ml of methanol were dissolved 300 mg of methyl 3-[4-methoxy-3-[N-(4-trifluoromethylbenzyl)]carbamoylphenyl]-2-(methylsulfonyl)propionate, 0.7 ml of 1 mol/l aqueous solution of sodium hydroxide were added, and the mixture was stirred for 1 hour at 50° C. The reaction mixture was poured into water and washed with diethyl ether. The aqueous layer was adjusted to pH value of 1 to 2 with 2 mol/l aqueous solution of hydrochloric acid, which was extracted with methylene chloride. The organic layer was washed with water and saturated brine in sequence and dried over anhydrous sodium sulfate. Solvent was distilled off under reduced pressure, and the crystals obtained were recrystallized from diethyl ether-ethyl acetate to obtain 218 mg of aimed product as colorless crystals.

Workup

additionwere added
washwashed with diethyl ether
extractionwas extracted with methylene chloride
washThe organic layer was washed with water and saturated brine in sequence
dry with materialdried over anhydrous sodium sulfate
distillationSolvent was distilled off under reduced pressure
customthe crystals obtained
customwere recrystallized from diethyl ether-ethyl acetate

Sources & evidence

ORD record: ord-0c630759926242ef94b950911f87a8af
Source dataset: uspto-grants-2004_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06706763B1

Reaction notes

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