(alpha,alpha,alpha-Trifluoro-4-tolyl)acetic acid → 2-{4-[2-(4-Trifluoromethyl-phenyl)-acetoxymethyl]phenylsulfanylmethyl}benzoic acid 2,2,2-trichloro-ethyl ester

HRID 1628170

反応式

HRID 1628170 の反応式
[Cl:1][C:2]([Cl:24])([Cl:23])[CH2:3][O:4][C:5](=[O:22])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[CH2:12][S:13][C:14]1[CH:19]=[CH:18][C:17]([CH2:20][OH:21])=[CH:16][CH:15]=1.[F:25][C:26]([F:38])([F:37])[C:27]1[CH:32]=[CH:31][C:30]([CH2:33][C:34](O)=[O:35])=[CH:29][CH:28]=1>CN(C1C=CN=CC=1)C.C(Cl)Cl>[Cl:24][C:2]([Cl:1])([Cl:23])[CH2:3][O:4][C:5](=[O:22])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[CH2:12][S:13][C:14]1[CH:19]=[CH:18][C:17]([CH2:20][O:21][C:34](=[O:35])[CH2:33][C:30]2[CH:29]=[CH:28][C:27]([C:26]([F:37])([F:25])[F:38])=[CH:32][CH:31]=2)=[CH:16][CH:15]=1

参加物

5

反応物 2

HCID 118342(alpha,alpha,alpha-Trifluoro-4-tolyl)acetic acidHCID 668652542-(4-Hydroxymethyl-phenylsulfanylmethyl)-benzoic acid 2,2,2-trichloro-ethyl ester2 回

生成物 1

HCID 866503092-{4-[2-(4-Trifluoromethyl-phenyl)-acetoxymethyl]phenylsulfanylmethyl}benzoic acid 2,2,2-trichloro-ethyl ester収率 109.4%

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒2 回HCID 6344Dichloromethane溶媒2 回

実験手順

2-(4-Hydroxymethyl-phenylsulfanylmethyl)-benzoic acid 2,2,2-trichloro-ethyl ester (70 mg, 0.173 mmol) was added to a stirred mixture of (4-trifluoromethyl-phenyl) acetic acid (39 mg, 0.190 mmol), EDCxHCl (50 mg, 0.259 mmol), DMAP (2.1 mg, 0.017 mmol) and DCM (3 mL). The reaction mixture was stirred at rt overnight, according to LC-MS analysis the reaction was uncomplete. Additional EDCxHCl (50 mg, 0.259 mmol), DMAP (2.1 mg, 0.017 mmol) and 2-(4-hydroxymethyl-phenylsulfanylmethyl)-benzoic acid 2,2,2-trichloro-ethyl ester (70 mg, 0.173 mmol) were added and the mixture was stirred for 3 h. More DCM was added and the mixture was washed with 0.25M HCl, the organic portion was dried through a phase separator and concentrated to give the titled compound (112 mg, 100%); Mass spectrum: M−H+ 590.

後処理

  1. stirringthe mixture was stirred for 3 h
  2. washthe mixture was washed with 0.25M HCl
  3. customthe organic portion was dried through a phase separator
  4. concentrationconcentrated

出典と根拠

ORDレコード
ord-ae8a677fd9804cb785e926c4362f079a
出典データセット
uspto-grants-2014_07
特許番号
US08785681B2

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