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2-Benzylsulfanylmethylacrylic acid → 2-Benzylsulfanylmethyl-3-[2-(1,1-difluoro-methoxy)-benzylsulfanyl]-propionic acid

HRID 1830119
ノート
印刷プレビュー

反応式

HRID 1830119 の反応式
[F:1][CH:2]([F:12])[O:3][C:4]1[CH:11]=[CH:10][CH:9]=[CH:8][C:5]=1[CH2:6][SH:7].[CH2:13]([S:20][CH2:21][C:22](=[CH2:26])[C:23]([OH:25])=[O:24])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>CN(C)C1C=CN=CC=1.CN(C=O)C>[CH2:13]([S:20][CH2:21][CH:22]([CH2:26][S:7][CH2:6][C:5]1[CH:8]=[CH:9][CH:10]=[CH:11][C:4]=1[O:3][CH:2]([F:12])[F:1])[C:23]([OH:25])=[O:24])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 2

HCID 220539822-Benzylsulfanylmethylacrylic acidHCID 22054104[2-(Difluoromethoxy)phenyl]methanethiol2 回

生成物 1

HCID 220539802-Benzylsulfanylmethyl-3-[2-(1,1-difluoro-methoxy)-benzylsulfanyl]-propionic acid収率 63%

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6228Dimethylformamide溶媒

実験手順

A solution of 2-difluoromethoxybenzyl mercaptan (0.534 g, 2.81 mmol), 2-benzylsulfanylmethyl-acrylic acid (0.585 g, 2.81 mmol) and 4-dimethylaminopyridine (36 mg, 0.3 mmol) in DMF (1.5 ml) was stirred at room temperature for 20 hours. An additional amount of 2-difluoromethoxybenzyl mercaptan (0.201 g) was added to the reaction mixture and stirring was continued for another 24 hours. The reaction mixture was poured into dilute, cold, aqueous HCl and the product extracted with ethyl acetate. The extracts were washed with saturated aqueous sodium chloride and then dried over magnesium sulfate. The solvent was removed by rotary evaporation at reduced pressure and the residue was chromatographed on silica gel eluting with ethyl acetate/hexane to give 2-Benzylsulfanylmethyl-3-[2-(1,1-difluoro-methoxy)-benzylsulfanyl]-propionic acid (0.706 g).

後処理

  1. additionThe reaction mixture was poured
  2. additioninto dilute
  3. extractioncold, aqueous HCl and the product extracted with ethyl acetate
  4. washThe extracts were washed with saturated aqueous sodium chloride
  5. dry with materialdried over magnesium sulfate
  6. customThe solvent was removed by rotary evaporation at reduced pressure
  7. customthe residue was chromatographed on silica gel eluting with ethyl acetate/hexane

出典と根拠

ORDレコード
ord-78f659bb8cf445b49e76319e3f6c517f
出典データセット
uspto-grants-2006_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07064123B1

反応ノート

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