Sodium hydride → 1-[4'-(3-Methyl-4-phenethylsulfanylmethyl-isoxazol-5-yl)-biphenyl-4-yl]-cyclopropanecarboxylic acid ethyl ester

HRID 1528776ノート

反応式

HRID 1528776 の反応式
[H-].[Na+].[CH2:3]([O:5][C:6]([C:8]1([C:11]2[CH:16]=[CH:15][C:14]([C:17]3[CH:22]=[CH:21][C:20]([C:23]4[O:27][N:26]=[C:25]([CH3:28])[C:24]=4[CH2:29]Br)=[CH:19][CH:18]=3)=[CH:13][CH:12]=2)[CH2:10][CH2:9]1)=[O:7])[CH3:4].[C:31]1([CH2:37][CH2:38][SH:39])[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1>CN(C=O)C>[CH2:3]([O:5][C:6]([C:8]1([C:11]2[CH:16]=[CH:15][C:14]([C:17]3[CH:22]=[CH:21][C:20]([C:23]4[O:27][N:26]=[C:25]([CH3:28])[C:24]=4[CH2:29][S:39][CH2:38][CH2:37][C:31]4[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=4)=[CH:19][CH:18]=3)=[CH:13][CH:12]=2)[CH2:10][CH2:9]1)=[O:7])[CH3:4]

参加物

5

反応物 3

HCID 24758Sodium hydrideHCID 781262-PhenylethanethiolHCID 665771991-[4'-(4-Bromomethyl-3-methyl-isoxazol-5-yl)-biphenyl-4-yl]-cyclopropanecarboxylic acid ethyl ester

生成物 1

HCID 665772021-[4'-(3-Methyl-4-phenethylsulfanylmethyl-isoxazol-5-yl)-biphenyl-4-yl]-cyclopropanecarboxylic acid ethyl ester

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

Sodium hydride (60% in mineral oil, 0.070 g, 1.70 mmol) was added to a solution of 1-[4′-(4-bromomethyl-3-methyl-isoxazol-5-yl)-biphenyl-4-yl]-cyclopropanecarboxylic acid ethyl ester (0.500 g, 1.13 mmol) and 2-phenylethanethiol (0.15 mL, 1.13 mmol) in DMF. The reaction was stirred at room temperature for 2 hours, and then partitioned between EtOAc and H2O and acidified with 1 N aqueous HCl. The aqueous layer was extracted with EtOAc, and the combined organic layers were dried over MgSO4, filtered, and concentrated. Analytical LCMS indicated that a mixture of the title compound and the hydrolyzed acid were present, so the crude material was used directly in the hydrolysis step.

後処理

  1. custompartitioned between EtOAc and H2O
  2. extractionThe aqueous layer was extracted with EtOAc
  3. dry with materialthe combined organic layers were dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. additionAnalytical LCMS indicated that a mixture of the title compound
  7. customwas used directly in the hydrolysis step

出典と根拠

ORDレコード
ord-7b71e9a5590b4a929e83675e0e32fcbd
出典データセット
uspto-grants-2015_07
特許番号
US09090573B2

反応ノート

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