Ethyl 3-{[5-(biphenyl-4-yl)-4,6-difluoro-1H-benzimidazol-2-yl]oxy}cyclobutane carboxylate → 3-{[5-(biphenyl-4-yl)-4,6-difluoro-1H-benzimidazol-2-yl]oxy}cyclo-butanecarboxylic acid

HRID 340797ノート

反応式

HRID 340797 の反応式
[C:1]1([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH:6]=[CH:5][C:4]([C:7]2[C:25]([F:26])=[CH:24][C:10]3[NH:11][C:12]([O:14][CH:15]4[CH2:18][CH:17]([C:19]([O:21]CC)=[O:20])[CH2:16]4)=[N:13][C:9]=3[C:8]=2[F:27])=[CH:3][CH:2]=1.O([Si](C)(C)C)[K]>C1COCC1.CCOC(C)=O>[C:1]1([C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)[CH:2]=[CH:3][C:4]([C:7]2[C:25]([F:26])=[CH:24][C:10]3[NH:11][C:12]([O:14][CH:15]4[CH2:18][CH:17]([C:19]([OH:21])=[O:20])[CH2:16]4)=[N:13][C:9]=3[C:8]=2[F:27])=[CH:5][CH:6]=1

参加物

5

反応物 2

HCID 67405225Ethyl 3-{[5-(biphenyl-4-yl)-4,6-difluoro-1H-benzimidazol-2-yl]oxy}cyclobutane carboxylateHCID 178504318HCID 178504318、化合物

生成物 1

HCID 533723763-{[5-(biphenyl-4-yl)-4,6-difluoro-1H-benzimidazol-2-yl]oxy}cyclo-butanecarboxylic acid

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

Ethyl 3-{[5-(biphenyl-4-yl)-4,6-difluoro-1H-benzimidazol-2-yl]oxy}cyclobutane carboxylate (0.046 g, 0.102 mmol) was dissolved in 1 mL of THF and treated with KOTMS (0.039 g, 0.308 mmol). The reaction mixture was stirred at ambient temperature overnight, and then diluted with EtOAc and washed with 2 N HCl. The aqueous layer was further extracted with EtOAc, and the combined organic layers were washed with brine, dried over Na2SO4, filtered, and concentrated to give the title compound. LCMS: calculated for C24H18F2N2O3 420.41, observed m/e 420.9 (M+H)+ (Rt 2.07/4 min). 1H NMR (500 MHz, d6-DMSO): δ7.77 (d, 2H), 7.73, (d, 2H), 7.55-7.47 (m, 4H), 7.39 (m, 1H), 7.15 (br, 1H), 5.23 (m, 1H), 2.82-2.70 (m, 2H), 2.32-2.25 (m, 2H), 1.98 (m, 1H).

後処理

  1. washwashed with 2 N HCl
  2. extractionThe aqueous layer was further extracted with EtOAc
  3. washthe combined organic layers were washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

出典と根拠

ORDレコード
ord-248cfed5d7db445aab79a93c099c6a10
出典データセット
uspto-grants-2014_11
特許番号
US08895596B2

反応ノート

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