Water → 4-(2-Hydroxy-2-methylpropylamino)benzenesulfonic acid 2-tert-butoxycarbonylaminobenzothiazol-6-yl ester

HRID 1867995Notes

Reaction equation

HRID 1867995 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].C(=O)([O-])[O-].[Cs+].[Cs+].[NH2:35][CH2:36][C:37]([CH3:40])([OH:39])[CH3:38].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:35][CH2:36][C:37]([OH:39])([CH3:40])[CH3:38])=[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 10796Cesium carbonateHCID 951022-Propanol, 1-amino-2-methyl-HCID 579808604-Fluorobenzenesulfonic acid 2-tert-butoxycarbonylaminobenzo-thiazol-6-yl ester2×

Product 1

HCID 579808624-(2-Hydroxy-2-methylpropylamino)benzenesulfonic acid 2-tert-butoxycarbonylaminobenzothiazol-6-yl esterYield 83.1%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A solution of 4-fluorobenzenesulfonic acid 2-tert-butoxycarbonylaminobenzo-thiazol-6-yl ester (intermediate 15) (300 mg, 0.707 mmol), cesium carbonate (230 mg, 0.707 mmol) and 1-amino-2-methylpropan-2-ol (126 mg, 1.414 mmol) in 5 ml of dimethyl sulfoxide is stirred at 80° C. for 72 hours. Water is added to the reaction medium, and the mixture is extracted 3 times with ethyl acetate. The organic phase is washed with saturated sodium chloride solution and then dried over magnesium sulfate and finally evaporated to dryness to give 290 mg of 4-(2-hydroxy-2-methylpropylamino)benzenesulfonic acid 2-tert-butoxycarbonylaminobenzo-thiazol-6-yl ester in a yield of 83%.

Workup

  1. extractionthe mixture is extracted 3 times with ethyl acetate
  2. washThe organic phase is washed with saturated sodium chloride solution
  3. dry with materialdried over magnesium sulfate
  4. customfinally evaporated to dryness

Sources & evidence

ORD record
ord-4393ab1103144b0db1f37020b8ec58ce
Source dataset
uspto-grants-2009_12
Patent number
US07632952B2

Reaction notes

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