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2-(tert-Butyldimethylsilyl)-N,N-dimethyl-1H-imidazole-1-sulfonamide → Rac-7-{[2-(tert-butyl-dimethyl-silanyl)-1-dimethylsulfamoyl-1h-imidazol-4-yl]-hydroxy-methyl}-5-methyl-benzofuran-2-carboxylic acid ethyl ester

HRID 1694794
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HRID 1694794 반응식
[CH3:1][N:2]([CH3:18])[S:3]([N:6]1[CH:10]=[CH:9][N:8]=[C:7]1[Si:11]([C:14]([CH3:17])([CH3:16])[CH3:15])([CH3:13])[CH3:12])(=[O:5])=[O:4].[CH2:19]([O:21][C:22]([C:24]1[O:25][C:26]2[C:32]([CH:33]=[O:34])=[CH:31][C:30]([CH3:35])=[CH:29][C:27]=2[CH:28]=1)=[O:23])[CH3:20]>C1COCC1.CCCCCCC>[CH2:19]([O:21][C:22]([C:24]1[O:25][C:26]2[C:32]([CH:33]([C:9]3[N:8]=[C:7]([Si:11]([C:14]([CH3:15])([CH3:17])[CH3:16])([CH3:13])[CH3:12])[N:6]([S:3](=[O:4])(=[O:5])[N:2]([CH3:18])[CH3:1])[CH:10]=3)[OH:34])=[CH:31][C:30]([CH3:35])=[CH:29][C:27]=2[CH:28]=1)=[O:23])[CH3:20]
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참가 물질

5

반응물 2

HCID 64202092-(tert-Butyldimethylsilyl)-N,N-dimethyl-1H-imidazole-1-sulfonamideHCID 589519217-Formyl-5-methyl-benzofuran-2-carboxylic acid ethyl ester

생성물 1

HCID 58951952Rac-7-{[2-(tert-butyl-dimethyl-silanyl)-1-dimethylsulfamoyl-1h-imidazol-4-yl]-hydroxy-methyl}-5-methyl-benzofuran-2-carboxylic acid ethyl ester

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매2회
HCID 8900
Heptane
용매

실험 절차

A solution of 2-(tert-butyl-dimethyl-silanyl)-imidazole-1-sulfonic acid dimethylamide (1.0 g) in THF (10 ml) was cooled under an Argon atmosphere to −78° C. n-Buthyllithium solution (1.6 M in heptane, 2.37 ml) were added dropwise. After stirring for 1 hr at −78° C. a solution of 7-formyl-5-methyl-benzofuran-2-carboxylic acid ethyl ester (963 mg) in THF (10 ml) was added dropwise. Stirring was continued for 15 min at −78° C., then the reaction mixture was warmed up to r.t. overnight. After quenching with water, the mixture was extracted with EtOAc. The organics were dried over MgSO4, filtrated and concentrated. The crude product was purified by column chromatography (silica gel; gradient: cyclohexane→cyclohexane/EtOAc 1:1) to give rac-7-{[2-(tert-butyl-dimethyl-silanyl)-1-dimethylsulfamoyl-1H-imidazol-4-yl]-hydroxy-methyl}-5-methyl-benzofuran-2-carboxylic acid ethyl ester as light yellow amorphous solid; MS (ISP): 522.3 ((M+H)+.).

후처리

  1. additionwere added dropwise
  2. additionwas added dropwise
  3. customAfter quenching with water
  4. extractionthe mixture was extracted with EtOAc
  5. dry with materialThe organics were dried over MgSO4
  6. filtrationfiltrated
  7. concentrationconcentrated
  8. customThe crude product was purified by column chromatography (silica gel; gradient: cyclohexane→cyclohexane/EtOAc 1:1)

출처 및 근거

ORD 기록
ord-928f8e0546c844bd81bca93d307fdc4f
출처 데이터셋
uspto-grants-2012_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08158668B2

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