Water → 4-Isobutylaminobenzenesulfonic acid 2-tert-butoxycarbonylaminobenzothiazol-6-yl ester

HRID 1867970Notes

Reaction equation

HRID 1867970 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1[S:10][C:11]2[CH:17]=[C:16]([O:18][S:19]([C:22]3[CH:27]=[CH:26][C:25](F)=[CH:24][CH:23]=3)(=[O:21])=[O:20])[CH:15]=[CH:14][C:12]=2[N:13]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:29]([NH2:33])[CH:30]([CH3:32])[CH3:31].C(=O)([O-])[O-].[Cs+].[Cs+].O>CS(C)=O>[C:1]([O:5][C:6]([NH:8][C:9]1[S:10][C:11]2[CH:17]=[C:16]([O:18][S:19]([C:22]3[CH:27]=[CH:26][C:25]([NH:33][CH2:29][CH:30]([CH3:32])[CH3:31])=[CH:24][CH:23]=3)(=[O:21])=[O:20])[CH:15]=[CH:14][C:12]=2[N:13]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 6558IsobutylamineHCID 10796Cesium carbonateHCID 579808604-Fluorobenzenesulfonic acid 2-tert-butoxycarbonylaminobenzo-thiazol-6-yl ester2×

Product 1

HCID 579808634-Isobutylaminobenzenesulfonic acid 2-tert-butoxycarbonylaminobenzothiazol-6-yl esterYield 80%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A solution of 4-fluorobenzenesulfonic acid 2-tert-butoxycarbonylamino-benzothiazol-6-yl ester (intermediate 15) (1 g, 2.32 mmol), isobutylamine (517 mg, 7.07 mmol) and cesium carbonate (845 mg, 2.59 mmol) in 12 ml of DMSO is stirred at 80° C. overnight. 60 ml of water are added to the reaction medium. The mixture is extracted with ethyl acetate. The organic phase is washed with water and with saturated sodium chloride solution, dried over magnesium sulfate and then evaporated to dryness. The residue is washed with ethyl ether to give 880 mg of 4-isobutylaminobenzenesulfonic acid 2-tert-butoxycarbonylaminobenzothiazol-6-yl ester (beige-colored solid) in a yield of 80%.

Workup

  1. extractionThe mixture is extracted with ethyl acetate
  2. washThe organic phase is washed with water and with saturated sodium chloride solution
  3. dry with materialdried over magnesium sulfate
  4. customevaporated to dryness
  5. washThe residue is washed with ethyl ether

Sources & evidence

ORD record
ord-81e26419ba564bff8b0a7a279c35b70b
Source dataset
uspto-grants-2009_12
Patent number
US07632952B2

Reaction notes

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