HCID 9906481, compound → HCID 9885682, compound

HRID 1274439Notes

Reaction equation

[CH3:1][C:2]1([C:21]([F:24])([F:23])[F:22])[O:6][C:5](=[O:7])[N:4]([C:8]2[CH:15]=[CH:14][C:11]([C:12]#[N:13])=[C:10]([C:16]([F:19])([F:18])[F:17])[CH:9]=2)[C:3]1=[O:20].C(O)C.[OH2:28]>>[C:12]([C:11]1[CH:14]=[CH:15][C:8]([N:4]([C:3](=[O:20])[C:2]([OH:6])([CH3:1])[C:21]([F:22])([F:23])[F:24])[C:5](=[O:7])[OH:28])=[CH:9][C:10]=1[C:16]([F:17])([F:19])[F:18])#[N:13]

Participants

Reactant 2

HCID 9906481HCID 9906481, compound

HCID 19096565Water ethanol

Product 1

HCID 9885682HCID 9885682, compoundYield 17%

Procedure

100 mg of 4-(5-methyl-2,4-dioxo-5-(trifluoromethyl)oxazolidin-3-yl)-2-(trifluoromethyl)-benzonitrile, as prepared in Example 1, were dissolved in 20 ml of a 7/3 ethanol/water mixture and stirred for 5 days at room temperature. The reaction mixture was evaporated to dryness and then purified by chromatography on an RP18 silica column (eluent: 6/4 water/acetonitrile). 18 mg of (4-cyano-3-(trifluoromethyl)phenyl)(3,3,3-trifluoro-2-hydroxy-2-methylpropionyl)carbamic acid were obtained, for a yield of 17%.

Workup

customThe reaction mixture was evaporated to dryness
custompurified by chromatography on an RP18 silica column (eluent: 6/4 water/acetonitrile)

Sources & evidence

ORD record: ord-400686c68090492c8fd92c42e1bfb314
Source dataset: uspto-grants-2000_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06156899

Reaction notes

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