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

HRID 1830119
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HRID 1830119 반응식
[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
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 2

HCID 220539822-Benzylsulfanylmethylacrylic acidHCID 22054104[2-(Difluoromethoxy)phenyl]methanethiol2회

생성물 1

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

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 6228Dimethylformamide용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-78f659bb8cf445b49e76319e3f6c517f
출처 데이터셋
uspto-grants-2006_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07064123B1

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