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

HRID 340793ノート

反応式

HRID 340793 の反応式
[C:1]1([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH:6]=[CH:5][C:4]([C:7]2[C:26]([F:27])=[CH:25][C:10]3[NH:11][C:12]([O:14][CH:15]4[CH2:19][CH2:18][CH:17]([C:20]([O:22]CC)=[O:21])[CH2:16]4)=[N:13][C:9]=3[C:8]=2[F:28])=[CH:3][CH:2]=1.O([Si](C)(C)C)[K]>C1COCC1.CCOC(C)=O>[C:1]1([C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=2)[CH:2]=[CH:3][C:4]([C:7]2[C:26]([F:27])=[CH:25][C:10]3[NH:11][C:12]([O:14][CH:15]4[CH2:19][CH2:18][CH:17]([C:20]([OH:22])=[O:21])[CH2:16]4)=[N:13][C:9]=3[C:8]=2[F:28])=[CH:5][CH:6]=1

参加物

5

反応物 2

HCID 67406155Ethyl 3-{[5-(biphenyl-4-yl)-4,6-difluoro-1H-benzimidazol-2-yl]oxy}cyclopentanecarboxylateHCID 178504318HCID 178504318、化合物

生成物 1

HCID 533723783-{[5-(biphenyl-4-yl)-4,6-difluoro-1H-benzimidazol-2-yl]oxy}cyclo-pentanecarboxylic 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}cyclopentanecarboxylate (0.039 g, 0.084 mmol) was dissolved in 1 mL of THF and treated with KOTMS (0.032 g, 0.253 mmol). The reaction mixture was stirred overnight at ambient temperature, and then diluted with EtOAc and washed with 2 N HCl. The layers were separated and the aqueous layer was further extracted with EtOAc. The combined organic layers were washed with brine, dried over Na2SO4, filtered, and concentrated to afford the title compound as a white solid. LCMS: calculated for C25H20F2N2O3 434.43, observed m/e 434.9 (M+H)+ (Rt 2.24/4 min). 1H NMR (500 MHz, d6-DMSO): δ7.77 (d, 2H), 7.73 (d, 2H), 7.56-7.46 (m, 4H), 7.39 (m, 111), 7.14 (d, 1H), 5.50 (m, 1H), 2.95 (m, 1H), 2.20-1.80 (m, 6H).

後処理

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

出典と根拠

ORDレコード
ord-be5e999678c0489b993412ddfd601f19
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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