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

HRID 2386878ノート

反応式

HRID 2386878 の反応式
[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]

参加物

4

反応物 2

HCID 516892Sodium BicarbonateHCID 666970155-[2-(2-Chloro-5-methoxy-phenyl)-1-hydroxy-1-trifluoromethyl-propyl]-3-methyl-3H-benzooxazol-2-one

生成物 1

HCID 666970495-[2-(2-Chloro-5-hydroxy-phenyl)-1-hydroxy-1-trifluoromethyl-propyl]-3-methyl-3H-benzooxazol-2-one収率 67%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

反応条件

温度
0 °C

実験手順

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)−].

後処理

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

出典と根拠

ORDレコード
ord-1b29f79c4ec84c5d9da58e46e02d5d40
出典データセット
uspto-grants-2012_09
特許番号
US08268820B2

反応ノート

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