Triethylamine → Methanesulfonyloxy(4-methanesulfonyloxyphenyl)-acetic acid methyl ester

HRID 2306617

반응식

HRID 2306617 반응식
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[OH:6][C:7]1[CH:19]=[CH:18][C:10]([CH:11]([OH:17])[C:12]([O:14][CH2:15]C)=[O:13])=[CH:9][CH:8]=1.C(N(CC)CC)C>CN(C=O)C.O>[CH3:15][O:14][C:12](=[O:13])[CH:11]([O:17][S:2]([CH3:1])(=[O:4])=[O:3])[C:10]1[CH:18]=[CH:19][C:7]([O:6][S:2]([CH3:1])(=[O:4])=[O:3])=[CH:8][CH:9]=1

참가 물질

6

반응물 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 111357Benzeneacetic acid, alpha,4-dihydroxy-, ethyl ester

생성물 1

HCID 88018735Methanesulfonyloxy(4-methanesulfonyloxyphenyl)-acetic acid methyl ester

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

Methanesulfonyl chloride (0.395 ml, 5.10 mmol) is added dropwise at 0° C. to ethyl 4-hydroxymandelate (0.500 g, 2.55 mmol) and triethylamine (0.889 ml, 6.38 mmol) in DMF (5 ml) and the mixture is allowed to warm to room temperature overnight. The reaction mixture is diluted with water and extracted with ethyl acetate. The extract is washed with brine, dried (MgSO4), and evaporated to give oily residue which is purified by flash column chromatography (30% EtOAc/Hexane) (0.75 g, 82%). MS (m/z): [M+H]+=353.

후처리

  1. extractionextracted with ethyl acetate
  2. washThe extract is washed with brine
  3. dry with materialdried (MgSO4)
  4. customevaporated
  5. customto give oily residue which
  6. customis purified by flash column chromatography (30% EtOAc/Hexane) (0.75 g, 82%)

출처 및 근거

ORD 기록
ord-0f02e586205a4cb9b87e93177351fb27
출처 데이터셋
uspto-grants-2004_12
특허 번호
US06828317B2

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