2-Propanesulfonyl chloride → Isopropylsulphonic acid-(4-tert.butoxycarbonylamino-phenyl)-amide

HRID 24939

Reaction equation

HRID 24939 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

HCID 824082-Propanesulfonyl chlorideHCID 688611tert-Butyl (4-aminophenyl)carbamate

Product 1

HCID 22569426Isopropylsulphonic acid-(4-tert.butoxycarbonylamino-phenyl)-amide

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

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).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic phases are washed with water
  3. customThe residue is chromatographed on silica gel (dichloromethane/methanol/NH4OH=19:1:0.1)

Sources & evidence

ORD record
ord-da9825c092654534b8c9572e9d0b2491
Source dataset
uspto-grants-2005_02
Patent number
US06855710B2

Linked notes

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