tert-Butanol → HCID 66816414, compound

HRID 1754957Notes

Reaction equation

HRID 1754957 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[CH:19]=[CH:18][C:17](/[CH:20]=[CH:21]/[S:22]([N:25]2[CH2:46][CH2:45][C:28]3([N:32]=[C:31]([C:33]4[CH:38]=[CH:37][CH:36]=[C:35]([O:39][C:40]([F:43])([F:42])[F:41])[CH:34]=4)[NH:30][C:29]3=[O:44])[CH2:27][CH2:26]2)(=[O:24])=[O:23])=[C:16]([CH3:47])[CH:15]=1.C(N(CC)CC)C>ClCCl>[C:1]([O:5][C:11]([NH:10][S:7]([NH:13][C:14]1[CH:19]=[CH:18][C:17](/[CH:20]=[CH:21]/[S:22]([N:25]2[CH2:26][CH2:27][C:28]3([N:32]=[C:31]([C:33]4[CH:38]=[CH:37][CH:36]=[C:35]([O:39][C:40]([F:41])([F:43])[F:42])[CH:34]=4)[NH:30][C:29]3=[O:44])[CH2:45][CH2:46]2)(=[O:23])=[O:24])=[C:16]([CH3:47])[CH:15]=1)(=[O:9])=[O:8])=[O:12])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 6386tert-ButanolHCID 8471TriethylamineHCID 70918Chlorosulfonyl isocyanateHCID 66817879HCID 66817879, compound

Product 1

HCID 66816414HCID 66816414, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

A solution of tert-butanol (71.9 mg, 0.97 mmol) in dichloromethane (1.5 ml) was added to a solution of chlorosulfonyl isocyanate (137 mg, 0.97 mmol) in dichloromethane (3 ml) with stirring under ice-cooling. The mixture was stirred at 0° C. for 10 minutes. A solution of 8-[(E)-2-(4-amino-2-methyl-phenyl)-ethenesulfonyl]-2-(3-trifluoromethoxy-phenyl)-1,3,8-triaza-spiro[4.5]dec-1-en-4-one (400 mg, 0.81 mmol) and triethylamine (164 mg, 1.62 mmol) in dichloromethane (3 ml) was then added, and the mixture was further stirred for one hour. The mixed reaction solution was quenched with water and then extracted with dichloromethane. The organic layer was washed with saturated brine, and then dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (ethyl acetate-hexane) to give N-(tert-butoxycarbonyl)-N′-(3-methyl-4-{(E)-2-[4-oxo-2-(3-trifluoromethoxy-phenyl)-1,3,8-triaza-spiro[4.5]dec-1-ene-8-sulfonyl]-vinyl}-phenyl)sulfamide (334 mg, 60.0%).

Workup

  1. temperaturecooling
  2. stirringThe mixture was stirred at 0° C. for 10 minutes
  3. stirringthe mixture was further stirred for one hour
  4. customThe mixed reaction solution
  5. customwas quenched with water
  6. extractionextracted with dichloromethane
  7. washThe organic layer was washed with saturated brine
  8. dry with materialdried over anhydrous magnesium sulfate
  9. concentrationconcentrated under reduced pressure
  10. customThe resulting residue was purified by silica gel column chromatography (ethyl acetate-hexane)

Sources & evidence

ORD record
ord-16d3f4509892442a96473b9e5fadfa75
Source dataset
uspto-grants-2015_10
Patent number
US09169254B2

Reaction notes

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