Sodium Bicarbonate → 5-[2-(2-Chloro-5-hydroxy-phenyl)-1-hydroxy-1-trifluoromethyl-propyl]-3-methyl-3H-benzooxazol-2-one

HRID 2386878Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8]C)=[CH:4][C:3]=1[CH:10]([CH3:28])[C:11]([C:17]1[CH:18]=[CH:19][C:20]2[O:24][C:23](=[O:25])[N:22]([CH3:26])[C:21]=2[CH:27]=1)([OH:16])[C:12]([F:15])([F:14])[F:13].C([O-])(O)=O.[Na+]>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[CH:10]([CH3:28])[C:11]([C:17]1[CH:18]=[CH:19][C:20]2[O:24][C:23](=[O:25])[N:22]([CH3:26])[C:21]=2[CH:27]=1)([OH:16])[C:12]([F:13])([F:14])[F:15]

Participants

Conditions

Temperature: 0 °C

Procedure

5-[2-(2-Chloro-5-methoxy-phenyl)-1-hydroxy-1-trifluoromethyl-propyl]-3-methyl-3H-benzooxazol-2-one (34 mg, obtained in Example 192, step 3) was dissolved in CH2Cl2 (5 mL) and cooled to 0° C. Borontribromide (1M in CH2Cl2, 0.33 mL) was added over a period of 10 minutes. Stirring was continued for 1 hour at 0° C. The reaction mixture was poured into ice and basified with sat. NaHCO3 and extracted three times with CH2Cl2. The combined organic layers were washed with brine, dried over Na2SO4, filtered and the solvent was evaporated. The residue was purified by flash chromatography (silica gel, heptane:ethyl acetate=6:4) to give the title compound as a colorless amorphous foam (22 mg, 67%). MS (neg. ion, m/e)=400.1 [(M−H)−].

Workup

extractionextracted three times with CH2Cl2
washThe combined organic layers were washed with brine
dry with materialdried over Na2SO4
filtrationfiltered
customthe solvent was evaporated
customThe residue was purified by flash chromatography (silica gel, heptane:ethyl acetate=6:4)

Sources & evidence

ORD record: ord-1b29f79c4ec84c5d9da58e46e02d5d40
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08268820B2

Reaction notes

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