Methyl Thioglycolate → (3-Oxo-2-thiophen-2-ylmethyl-2,3-dihydro-1H-isoindol-1-ylsulfanyl)-acetic acid methyl ester

HRID 492228ノート

反応式

HRID 492228 の反応式
O[CH:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[N:3]1[CH2:12][C:13]1[S:14][CH:15]=[CH:16][CH:17]=1.[C:18]([O:22][CH3:23])(=[O:21])[CH2:19][SH:20].C(=O)(O)[O-].[Na+]>ClCCl>[CH3:23][O:22][C:18](=[O:21])[CH2:19][S:20][CH:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[N:3]1[CH2:12][C:13]1[S:14][CH:15]=[CH:16][CH:17]=1

参加物

5

反応物 3

HCID 16907Methyl ThioglycolateHCID 516892Sodium BicarbonateHCID 4616003HCID 4616003、化合物

生成物 1

HCID 57679339(3-Oxo-2-thiophen-2-ylmethyl-2,3-dihydro-1H-isoindol-1-ylsulfanyl)-acetic acid methyl ester収率 96%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a solution of 12 (500 mg, 2.04 mmol) in dichloromethane (15 mL) at room temperature was added methyl thioglycolate (204 μL, 2.24 mmol) and the resulting reaction mixture was stirred at room temperature for 18 hours in a sealed tube. The reaction mixture was poured onto saturated sodium bicarbonate and extracted with ethyl acetate (3×30 mL). The combined ethyl acetate extracts were dried over anhydrous sodium sulfate and concentrated in vacuo. Chromatography (SiO2, 5% EtOAc-Hexanes eluant) provided 650 mg of 13 as a white solid (679 mg theoretical, 96% yield).

後処理

  1. customthe resulting reaction mixture
  2. extractionextracted with ethyl acetate (3×30 mL)
  3. dry with materialThe combined ethyl acetate extracts were dried over anhydrous sodium sulfate
  4. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-3e41b0dcc5964f87ac7e00cd85c7f4ae
出典データセット
uspto-grants-2009_05
特許番号
US07531671B2

反応ノート

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