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tert-Butanol → N-[5-(N-tert-butoxycarbonylsulfamoylamino)-4,6-dimethyl-1-octylindolin-7-yl]-2,2-dimethylpropanamide

HRID 33599
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HRID 33599 반응식
[C:1]([OH:5])([CH3:4])([CH3:3])[CH3:2].Cl[S:7]([N:10]=[C:11]=[O:12])(=[O:9])=[O:8].[NH2:13][C:14]1[C:15]([CH3:39])=[C:16]2[C:20](=[C:21]([NH:24][C:25](=[O:30])[C:26]([CH3:29])([CH3:28])[CH3:27])[C:22]=1[CH3:23])[N:19]([CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH3:38])[CH2:18][CH2:17]2.C(N(CC)CC)C>C(Cl)Cl>[C:1]([O:5][C:11]([NH:10][S:7]([NH:13][C:14]1[C:15]([CH3:39])=[C:16]2[C:20](=[C:21]([NH:24][C:25](=[O:30])[C:26]([CH3:28])([CH3:29])[CH3:27])[C:22]=1[CH3:23])[N:19]([CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH3:38])[CH2:18][CH2:17]2)(=[O:9])=[O:8])=[O:12])([CH3:4])([CH3:3])[CH3:2]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 6386tert-ButanolHCID 8471TriethylamineHCID 70918Chlorosulfonyl isocyanateHCID 23075425N-(5-Amino-4,6-dimethyl-1-octylindolin-7-yl)-2,2-dimethylpropanamide

생성물 1

HCID 23075439N-[5-(N-tert-butoxycarbonylsulfamoylamino)-4,6-dimethyl-1-octylindolin-7-yl]-2,2-dimethylpropanamide

시약·촉매·용매 1

HCID 6344
Dichloromethane
용매
2회

실험 절차

tert-Butanol (0.85 mL) was dissolved in methylene chloride (17 mL) and chlorosulfonyl isocyanate (0.77 mL) was added at −18° C. The mixture was stirred at the same temperature for 30 min and N-(5-amino-4,6-dimethyl-1-octylindolin-7-yl)-2,2-dimethylpropanamide (1.66 g) and triethylamine (1.24 mL) were added. The mixture was further stirred at −5° C. for 30 min. Methylene chloride (50 mL) was added, and the mixture was washed successively with 10% aqueous citric acid, saturated aqueous sodium hydrogencarbonate, and then saturated brine (50 mL) and dried over sodium sulfate. Then, methylene chloride was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography to give the title compound as crystals (1.9 g).

후처리

  1. stirringThe mixture was further stirred at −5° C. for 30 min
  2. washthe mixture was washed successively with 10% aqueous citric acid, saturated aqueous sodium hydrogencarbonate
  3. dry with materialsaturated brine (50 mL) and dried over sodium sulfate
  4. customThen, methylene chloride was evaporated under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-bb2f4849cf9745ecbfbe67d605536b76
출처 데이터셋
uspto-grants-2008_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07429612B2

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