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

HRID 492228노트

반응식

HRID 492228 반응식
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

참가 물질

5

반응물 3

HCID 16907Methyl ThioglycolateHCID 516892Sodium BicarbonateHCID 4616003HCID 4616003, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-3e41b0dcc5964f87ac7e00cd85c7f4ae
출처 데이터셋
uspto-grants-2009_05
특허 번호
US07531671B2

반응 노트

불러오는 중…