Trifluoroacetic acid → 4-Cyclopropylethynyl-6-hydroxy-4-trifluoromethyl-1,4-dihydro-benzo [d][1,3]oxazin-2-one

HRID 29014Notes

Reaction equation

[CH:1]1([C:4]#[C:5][C:6]2([C:24]([F:27])([F:26])[F:25])[O:11][C:10](=[O:12])[NH:9][C:8]3[CH:13]=[CH:14][C:15]([O:17]COCCOC)=[CH:16][C:7]2=3)[CH2:3][CH2:2]1.FC(F)(F)C(O)=O>>[CH:1]1([C:4]#[C:5][C:6]2([C:24]([F:26])([F:27])[F:25])[O:11][C:10](=[O:12])[NH:9][C:8]3[CH:13]=[CH:14][C:15]([OH:17])=[CH:16][C:7]2=3)[CH2:3][CH2:2]1

Participants

Reactant 2

HCID 6422Trifluoroacetic acid

HCID 688005564-Cyclopropylethynyl-6-(2-methoxy-ethoxymethoxy)-4-trifluoromethyl-1,4-dihydro-benzo[d][1,3]oxazin-2-one

Product 1

HCID 114264734-Cyclopropylethynyl-6-hydroxy-4-trifluoromethyl-1,4-dihydro-benzo [d][1,3]oxazin-2-oneYield 96%

Procedure

To 150 mg (0.39 mmol) of 8 was added 2 mL of trifluoroacetic acid. The mixture was allowed to stir at room temperature for 2 hours. The reaction mixture was concentrated under reduced pressure, and the residue was purified by preparative thin layer chromatography (2 mm silica gel plate, E. Merck) using 5% methanol in dichloromethane to give 110 mg (0.37 mmol, 96%) of 9 as a colorless oil [LC-MS; M+H 298.1].

Workup

concentrationThe reaction mixture was concentrated under reduced pressure
customthe residue was purified by preparative thin layer chromatography (2 mm silica gel plate, E. Merck)

Sources & evidence

ORD record: ord-177e98ea4def436f989e3244efdd332d
Source dataset: uspto-grants-2008_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07420043B2

Reaction notes

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