Diethyl Pyrocarbonate → 2-(4-(trifluoromethyl)phenyl)-N-(2,3-dihydro-2-oxobenzo[d]oxazol-7-yl)acetamide

HRID 1505201Notes

Reaction equation

[F:1][C:2]([F:14])([F:13])[C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10]([OH:12])=O)=[CH:5][CH:4]=1.CCOC(OC(OCC)=O)=O.[NH2:26][C:27]1[C:35]2[O:34][C:33](=[O:36])[NH:32][C:31]=2[CH:30]=[CH:29][CH:28]=1>C1COCC1>[F:13][C:2]([F:1])([F:14])[C:3]1[CH:4]=[CH:5][C:6]([CH2:9][C:10]([NH:26][C:27]2[C:35]3[O:34][C:33](=[O:36])[NH:32][C:31]=3[CH:30]=[CH:29][CH:28]=2)=[O:12])=[CH:7][CH:8]=1

Participants

Conditions

Temperature: 80 °C

Procedure

4-trifluoromethylphenylacetic acid (453 mg, 2.2 mmol) was dissolved in 20 ml of THF and at 0° C. DEPC (0.43 ml, 1.3 equiv) and amine 1c (400 mg, 2.66 mmol) were added to the solution. The mixture was warmed at 80° C. overnight, then evaporated and the crude was dissolved in AcOEt (30 ml) and washed with water (1×20 ml) and brine. The organic phase was dried over sodium sulfate and concentrated under vacuum. The purification of the crude residue by chromatographic column using AcOEt 3/petroleum ether 7 as eluant gave 340 mg of a white solid. Yield=46% 1HNMR (DMSO, 200 MHz) δ 3.86 (2H, s), 6.86 (1H, d), 7.06 (1H, t), 7.58 (3H, m), 7.70 (2H, d, J=8.4 Hz), 10.32 (1H, bs), 8.73 (1H, bs), 11.80 (1H, bs); [M+1] 337.2 (C16H11F3N2O3 requires 336.3).

Workup

customevaporated
dissolutionthe crude was dissolved in AcOEt (30 ml)
washwashed with water (1×20 ml) and brine
dry with materialThe organic phase was dried over sodium sulfate
concentrationconcentrated under vacuum
customThe purification of the crude residue by chromatographic column

Sources & evidence

ORD record: ord-665dd0bb7f824ffcb40accb358ed5072
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09216975B2

Reaction notes

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