Water → HCID 86668195, compound

HRID 243802Notes

Reaction equation

[NH2:1][C:2]1[C:3]([O:18][CH3:19])=[C:4]([CH:12]([OH:17])[C:13]([F:16])([F:15])[F:14])[CH:5]=[C:6]([C:8]([CH3:11])([CH3:10])[CH3:9])[CH:7]=1.C(N(CC)C(C)C)(C)C.Cl[C:30]([O:32][CH2:33][C:34]([Cl:37])([Cl:36])[Cl:35])=[O:31].O>C1COCC1>[C:8]([C:6]1[CH:5]=[C:4]([CH:12]([OH:17])[C:13]([F:15])([F:16])[F:14])[C:3]([O:18][CH3:19])=[C:2]([NH:1][C:30](=[O:31])[O:32][CH2:33][C:34]([Cl:37])([Cl:36])[Cl:35])[CH:7]=1)([CH3:11])([CH3:10])[CH3:9]

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of crude product (0.397 g) containing 1-(3-amino-5-tert-butyl-2-methoxyphenyl)-2,2,2-trifluoroethanol and N,N-diisopropylethylamine (0.374 mL, 2.14 mmol) in THF (4.77 mL) was cooled to 0° C., and 2,2,2-trichloroethyl chloroformate (0.217 mL, 1.57 mmol) was added thereto, followed by stirring the mixture for 10 minutes. Water was added to the reaction solution and the aqueous layer was extracted with ethyl acetate and the organic layer was washed with saturated brine. The organic layer was dried over anhydrous sodium sulfate and filtered, and then the solvent was evaporated under reduced pressure. The obtained residue was purified by column chromatography (silica gel, hexane/ethyl acetate=100/0-75/25) to obtain 0.622 g of the captioned compound (96% yield in 2 steps).

Workup

extractionthe aqueous layer was extracted with ethyl acetate
washthe organic layer was washed with saturated brine
dry with materialThe organic layer was dried over anhydrous sodium sulfate
filtrationfiltered
customthe solvent was evaporated under reduced pressure
customThe obtained residue was purified by column chromatography (silica gel, hexane/ethyl acetate=100/0-75/25)

Sources & evidence

ORD record: ord-169bc8e0bf564498a76bac64825d7c9e
Source dataset: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08653304B2

Reaction notes

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