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Methanesulfonamide → [2-(7-(methanesulfonamidylcarbomethoxy)-1H-indol-3-yl)-1,1-dimethyl-ethyl]-carbamic acid tert-butyl ester

HRID 8126
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인쇄 미리보기

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HRID 8126 반응식
[CH3:1][S:2]([NH2:5])(=[O:4])=[O:3].C[Al](C)C.[C:10]([O:14][C:15](=[O:36])[NH:16][C:17]([CH3:35])([CH3:34])[CH2:18][C:19]1[C:27]2[C:22](=[C:23]([C:28]([O:30][CH2:31]OC)=[O:29])[CH:24]=[CH:25][CH:26]=2)[NH:21][CH:20]=1)([CH3:13])([CH3:12])[CH3:11]>ClCCl>[C:10]([O:14][C:15](=[O:36])[NH:16][C:17]([CH3:35])([CH3:34])[CH2:18][C:19]1[C:27]2[C:22](=[C:23]([C:28]([O:30][CH2:31][NH:5][S:2]([CH3:1])(=[O:4])=[O:3])=[O:29])[CH:24]=[CH:25][CH:26]=2)[NH:21][CH:20]=1)([CH3:12])([CH3:13])[CH3:11]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 72879MethanesulfonamideHCID 16682925TrimethylaluminumHCID 69517575[2-(7-(methoxycarbomethoxy)-1H-indol-3-yl)-1,1-dimethyl-ethyl]-carbamic acid tert-butyl ester

생성물 1

HCID 69518509[2-(7-(methanesulfonamidylcarbomethoxy)-1H-indol-3-yl)-1,1-dimethyl-ethyl]-carbamic acid tert-butyl ester수율 117.8%

시약·촉매·용매 1

HCID 6344
Dichloromethane
용매
2회

실험 절차

A solution of methanesulfonamide (106 mg, 1.12 mmol) and trimethyl aluminum (2.0 M in hexanes, 0.56 ml, 1.12 mmol) in dry dichloromethane (5.0 ml) is stirred at room temperature under a nitrogen atmosphere for 20 minutes. A solution of [2-(7-(methoxycarbomethoxy)-1H-indol-3-yl)-1,1-dimethyl-ethyl]-carbamic acid tert-butyl ester (160 mg, 0.425 mmol) in dry dichloromethane (1.5 ml) is added and the mixture is heated under reflux for 15 hours. The mixture is cooled to room temperature and quenched with 1 N HCl solution (3.4 ml) and partitioned between ethyl acetate and water. The organic extracts are dried over anhydrous Na2SO4, filtered and the solvent evaporated to give 220 mg of [2-(7-(methanesulfonamidylcarbomethoxy)-1H-indol-3-yl)-1,1-dimethyl-ethyl]-carbamic acid tert-butyl ester (90%).

후처리

  1. temperaturethe mixture is heated
  2. temperatureunder reflux for 15 hours
  3. customquenched with 1 N HCl solution (3.4 ml)
  4. custompartitioned between ethyl acetate and water
  5. dry with materialThe organic extracts are dried over anhydrous Na2SO4
  6. filtrationfiltered
  7. customthe solvent evaporated

출처 및 근거

ORD 기록
ord-d6abe5dd3fb941639e55b4abc3d4079d
출처 데이터셋
uspto-grants-2006_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07087635B2

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