反応式
C[O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:16]=[CH:15][C:14]([CH:17]([CH3:35])[C:18]([OH:34])([C:23]3[CH:33]=[CH:32][C:26]4[N:27]([CH3:31])[C:28](=[O:30])[O:29][C:25]=4[CH:24]=3)[C:19]([F:22])([F:21])[F:20])=[C:13]([Cl:36])[CH:12]=2)=[CH:7][C:6]=1[F:37])=[O:4].[Li+].[OH-].O>C1COCC1>[Cl:36][C:13]1[CH:12]=[C:11]([C:8]2[CH:9]=[CH:10][C:5]([C:3]([OH:4])=[O:2])=[C:6]([F:37])[CH:7]=2)[CH:16]=[CH:15][C:14]=1[CH:17]([CH3:35])[C:18]([OH:34])([C:23]1[CH:33]=[CH:32][C:26]2[N:27]([CH3:31])[C:28](=[O:30])[O:29][C:25]=2[CH:24]=1)[C:19]([F:22])([F:20])[F:21]参加物
反応物 3
生成物 1
試薬・触媒・溶媒 1
実験手順
3′-Chloro-3-fluoro-4′-[3,3,3-trifluoro-2-hydroxy-1-methyl-2-(3-methyl-2-oxo-2,3-dihydro-benzooxazol-6-yl)-propyl]-biphenyl-4-carboxylic acid methyl ester (60 mg, obtained in Example 134, step 1) was dissolved in THF (4 mL) followed by the addition of aqueous LiOH solution (1.0M, 0.145 mL). The mixture was stirred over night at r.t. The reaction mixture was poured into water and extracted with ethyl acetate. The aqueous phase was acidified with 2 M aqueous HCl to pH 1 and extracted three times with ethyl acetate. The combined organic layers were washed with brine, dried over Na2SO4 and the solvent was evaporated. The residue was purified by flash chromatography (silica gel, CH2Cl2:MeOH=7:3 to 1:1) to give the title compound as a brown solid (13 mg, 22%). MS (neg. ion, m/e)=522.2 [(M−H)−].
後処理
- extractionextracted with ethyl acetate
- extractionextracted three times with ethyl acetate
- washThe combined organic layers were washed with brine
- dry with materialdried over Na2SO4
- customthe solvent was evaporated
- customThe residue was purified by flash chromatography (silica gel, CH2Cl2:MeOH=7:3 to 1:1)
出典と根拠
- ORDレコード
- ord-aff8fabf38c944fb96753123f6649564
- 出典データセット
- uspto-grants-2012_09
- 特許番号
- US08268820B2
関連ノート
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