tert-Butanol → HCID 86614314, compound

HRID 1951765Notes

Reaction equation

HRID 1951765 reaction equation
Cl[S:2]([N:5]=[C:6]=[O:7])(=[O:4])=[O:3].[C:8]([OH:12])([CH3:11])([CH3:10])[CH3:9].CC[N:15]([CH:19]([CH3:21])[CH3:20])C(C)C.ClS(N=C=O)(=O)=O.[C:29](O)(C)([CH3:31])[CH3:30]>ClCCCl.O.C(Cl)Cl>[S:2]([NH2:15])([NH:5][C:6]([O:12][C:8]([CH3:11])([CH3:10])[CH3:9])=[O:7])(=[O:4])=[O:3].[NH2:15][C:19]1[CH:20]=[CH:31][CH:29]=[CH:30][CH:21]=1

Participants

7

Reactant 4

HCID 6386tert-ButanolHCID 70918Chlorosulfonyl isocyanateHCID 81531DiisopropylethylamineHCID 86600364HCID 86600364, compound

Product 1

HCID 86614314HCID 86614314, compound

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolvent3×HCID 21908982Water methylene chlorideSolvent

Procedure

To a solution of chlorosulfonyl isocyanate (1.5 eq) in anhydrous 1,2-dichloroethane (0.1-0.5 M) at 0° C. was added 1.5 eq of tert-butanol as a solution in anhydrous 1,2-dichloroethane (0.5 M). The mixture was allowed to warm to room temperature while stirring and was then cooled to 0° C. again. A suspension of aniline-ester from general procedure E (1.0 eq) in 1,2-dichloroethane (0.3-0.5 M) and 2.5 eq DIEA was cooled to 0° C. and the chlorosulfonyl isocyanate-tert-butanol mixture was added drop-wise while stirring. The mixture was stirred at room temperature for 1 hour, then diluted with water/CH2Cl2 and the layers separated. The organic layers were combined and washed with water and brine. The organic phase was then dried over Na2SO4, filtered, and the filtrate was concentrated and purified by silica gel chromatography to afford the aniline N-Boc sulfamide derivative.

Workup

  1. temperaturewas then cooled to 0° C. again
  2. temperaturewas cooled to 0° C.
  3. stirringwhile stirring
  4. stirringThe mixture was stirred at room temperature for 1 hour
  5. customthe layers separated
  6. washwashed with water and brine
  7. dry with materialThe organic phase was then dried over Na2SO4
  8. filtrationfiltered
  9. concentrationthe filtrate was concentrated
  10. custompurified by silica gel chromatography

Sources & evidence

ORD record
ord-4247a12141154b13a71261ca55cc0db9
Source dataset
uspto-grants-2013_03
Patent number
US08404731B2

Reaction notes

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