Water → 2-(3-Carboxymethyl-phenylsulfanylmethyl)-benzoic acid 2,2,2-trichloro-ethyl ester

HRID 709481

反応式

HRID 709481 の反応式
C(=O)([O-])[O-].[Cs+].[Cs+].[SH:7][C:8]1[CH:9]=[C:10]([CH2:14][C:15]([OH:17])=[O:16])[CH:11]=[CH:12][CH:13]=1.[Cl:18][C:19]([Cl:33])([Cl:32])[CH2:20][O:21][C:22](=[O:31])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[CH2:29]Br.O>CN(C=O)C>[Cl:18][C:19]([Cl:32])([Cl:33])[CH2:20][O:21][C:22](=[O:31])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[CH2:29][S:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([CH2:14][C:15]([OH:17])=[O:16])[CH:9]=1

参加物

6

反応物 4

HCID 962WaterHCID 10796Cesium carbonateHCID 35431562-(3-Mercaptophenyl)acetic acidHCID 668652492-Bromomethyl-benzoic acid 2,2,2-trichloro-ethyl ester

生成物 1

HCID 668648212-(3-Carboxymethyl-phenylsulfanylmethyl)-benzoic acid 2,2,2-trichloro-ethyl ester収率 100.1%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

Cesium carbonate (1.69 g, 5.20 mmol) was added to a mixture of 3-mercapto-phenylacetic acid (0.73 g, 4.33 mmol) and 2-bromomethyl-benzoic acid 2,2,2-trichloro-ethyl ester (1.50 g, 4.33 mmol) in DMF (25 mL). The mixture was stirred for 1 h at rt. Water was added and the mixture was washed with diethyl ether. The aqueous phase was made acidic (pH5-3) with 2M HCl and thereafter extracted with diethyl ether. The combined organic phases were dried (Na2SO4) and concentrated to give the titled compound (1.88 g, 100%); 1H NMR (400 MHz, CDCl3): δ 3.50 (s, 2H), 4.46 (s, 2H), 4.88 (s, 2H), 7.01-7.08 (m, 1H), 7.10-7.16 (m, 4H), 7.22-7.35 (m, 2H), 8.00 (d, 1H); Mass spectrum: M−H+ 432.

後処理

  1. washthe mixture was washed with diethyl ether
  2. extractionextracted with diethyl ether
  3. dry with materialThe combined organic phases were dried (Na2SO4)
  4. concentrationconcentrated

出典と根拠

ORDレコード
ord-4262888bd99945ad9c28f0b8baffc439
出典データセット
uspto-grants-2015_11
特許番号
US09181181B2

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