Phosphorus oxychloride → Methyl 4-((1-(4-(5-tert-butyl-1,3-oxazol-2-yl)-2-methylphenyl)-4,4,4-trifluorobutyl)amino)benzoate

HRID 1520288Notes

Reaction equation

[CH3:1][C:2]([CH3:35])([CH3:34])[C:3](=[O:33])[CH2:4][NH:5][C:6]([C:8]1[CH:13]=[CH:12][C:11]([CH:14]([NH:21][C:22]2[CH:31]=[CH:30][C:25]([C:26]([O:28][CH3:29])=[O:27])=[CH:24][CH:23]=2)[CH2:15][CH2:16][C:17]([F:20])([F:19])[F:18])=[C:10]([CH3:32])[CH:9]=1)=O.P(Cl)(Cl)(Cl)=O>O>[C:2]([C:3]1[O:33][C:6]([C:8]2[CH:13]=[CH:12][C:11]([CH:14]([NH:21][C:22]3[CH:31]=[CH:30][C:25]([C:26]([O:28][CH3:29])=[O:27])=[CH:24][CH:23]=3)[CH2:15][CH2:16][C:17]([F:20])([F:19])[F:18])=[C:10]([CH3:32])[CH:9]=2)=[N:5][CH:4]=1)([CH3:34])([CH3:1])[CH3:35]

Participants

Conditions

Temperature: 90 °C

Procedure

To methyl 4-((1-(4-((3,3-dimethyl-2-oxobutyl)carbamoyl)-2-methylphenyl)-4,4,4-trifluorobutyl)amino)benzoate (200 mg) was added phosphoryl chloride (0.5 ml) at room temperature. The reaction mixture was heated at 90° C. for 1 hr, and water was added at room temperature. The filtrate was extracted with ethyl acetate, and the extract was washed with 1M aqueous sodium hydroxide solution and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated and the residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (155.4 mg).

Workup

extractionThe filtrate was extracted with ethyl acetate
washthe extract was washed with 1M aqueous sodium hydroxide solution and saturated brine
dry with materialdried over anhydrous magnesium sulfate
customThe solvent was evaporated
customthe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record: ord-e05d7a3efad748248fb71f755db1d5b7
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09073864B2

Reaction notes

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