Water → Phenyl 3-(2-fluoropropan-2-yl)isoxazol-5-ylcarbamate

HRID 929978Notes

Reaction equation

[F:1][C:2]([C:5]1[CH:9]=[C:8]([NH2:10])[O:7][N:6]=1)([CH3:4])[CH3:3].C([O-])([O-])=O.[K+].[K+].[C:17](Cl)(=[O:25])[O:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.O>C1COCC1>[F:1][C:2]([C:5]1[CH:9]=[C:8]([NH:10][C:17](=[O:25])[O:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[O:7][N:6]=1)([CH3:4])[CH3:3]

Participants

Conditions

Temperature: 0 °C

Procedure

To a mixture of 3-(2-fluoropropan-2-yl)isoxazol-5-amine (4.32 g, 0.03 mol) and K2CO3 (8.28 g, 0.06 mol) in THF (100 mL) at 0° C. was added dropwise a solution of phenyl carbonochloridate (6 mL, 0.045 mol) in THF (50 mL). The mixture was stirred at 0° C. for 1 h, then at 40° C. for 20 h. Analysis by LC-MS and TLC indicated that the starting material was almost completely consumed and a new product had formed. The mixture was poured into water (150 mL) and the resulting mixture was extracted with EtOAc (100 mL). The organic layer was dried over Na2SO4 and concentrated under reduced pressure. The residue was purified by silica gel chromatography eluting with 0-4% EtOAc in petroleum ether to afford phenyl 3-(2-fluoropropan-2-yl)isoxazol-5-ylcarbamate as a white solid (6 g, 76%).

Workup

waitat 40° C. for 20 h
customwas almost completely consumed
customa new product had formed
extractionthe resulting mixture was extracted with EtOAc (100 mL)
dry with materialThe organic layer was dried over Na2SO4
concentrationconcentrated under reduced pressure
customThe residue was purified by silica gel chromatography
washeluting with 0-4% EtOAc in petroleum ether

Sources & evidence

ORD record: ord-d63e6e52879e4b06bb21a551689e6869
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09296722B2

Reaction notes

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