2-Propanesulfonyl chloride → Isopropylsulphonic acid-(4-tert.butoxycarbonylamino-phenyl)-amide
Reaction equation
[CH:1]([S:4](Cl)(=[O:6])=[O:5])([CH3:3])[CH3:2].[C:8]([O:12][C:13]([NH:15][C:16]1[CH:22]=[CH:21][C:19]([NH2:20])=[CH:18][CH:17]=1)=[O:14])([CH3:11])([CH3:10])[CH3:9]>N1C=CC=CC=1>[C:8]([O:12][C:13]([NH:15][C:16]1[CH:17]=[CH:18][C:19]([NH:20][S:4]([CH:1]([CH3:3])[CH3:2])(=[O:6])=[O:5])=[CH:21][CH:22]=1)=[O:14])([CH3:11])([CH3:9])[CH3:10]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
1.2 g (10 mmol) of isopropylsulphonic acid chloride are added dropwise to a solution of 1.0 g (4.8 mmol) of 4-tert.butoxycarbonylamino-aniline in 10 ml of pyridine. The mixture is stirred for 18 hours at ambient temperature. Then the reaction solution is poured onto 150 ml of ice water and then extracted with ethyl acetate. The organic phases are washed with water and freed from solvent. The residue is chromatographed on silica gel (dichloromethane/methanol/NH4OH=19:1:0.1).