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

HRID 33599Notes

Reaction equation

HRID 33599 reaction equation
[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]

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-bb2f4849cf9745ecbfbe67d605536b76
Source dataset
uspto-grants-2008_09
Patent number
US07429612B2

Reaction notes

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