3-Nitrobenzenesulfonyl chloride → Ethyl 3-allyloxycarbonylamino-3-(3-[3-nitrophenylsulphonylamino]-phenyl)-propionate

HRID 968469Notes

Reaction equation

HRID 968469 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([S:10](Cl)(=[O:12])=[O:11])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].[CH2:14]([O:17][C:18]([NH:20][CH:21]([C:28]1[CH:33]=[CH:32][CH:31]=[C:30]([NH2:34])[CH:29]=1)[CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])=[O:19])[CH:15]=[CH2:16]>N1C=CC=CC=1>[CH2:14]([O:17][C:18]([NH:20][CH:21]([C:28]1[CH:33]=[CH:32][CH:31]=[C:30]([NH:34][S:10]([C:6]2[CH:7]=[CH:8][CH:9]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=2)(=[O:12])=[O:11])[CH:29]=1)[CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])=[O:19])[CH:15]=[CH2:16]

Participants

4

Reactant 2

HCID 84763-Nitrobenzenesulfonyl chlorideHCID 21101501Ethyl 3-allyloxycarbonylamino-3-(3-aminophenyl)-propionate

Product 1

HCID 21101499Ethyl 3-allyloxycarbonylamino-3-(3-[3-nitrophenylsulphonylamino]-phenyl)-propionate

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

3-Nitrophenylsulphonyl chloride was added at 0° C. to a solution of 11.6 g ethyl 3-{[(allyloxy)-carbonyl]-amino}-3-(3-aminophenyl)-propanoate from Example II.2.d in 110 ml of pyridine. After a reaction time of 2 h, the mixture was concentrated, 1 N hydrochloric acid was added, and the solution was extracted with dichloromethane. After drying the organic phase over magnesium sulphate, the solvent was removed and the crude product was purified by chromatography on silica gel (dichloromethane/methanol=40:1) to give 17.8 g of a solid.

Workup

  1. concentrationAfter a reaction time of 2 h, the mixture was concentrated
  2. addition1 N hydrochloric acid was added
  3. extractionthe solution was extracted with dichloromethane
  4. dry with materialAfter drying the organic phase over magnesium sulphate
  5. customthe solvent was removed
  6. customthe crude product was purified by chromatography on silica gel (dichloromethane/methanol=40:1)

Sources & evidence

ORD record
ord-28c86e642fa344579c18ed5d1971b588
Source dataset
uspto-grants-2007_12
Patent number
US07304037B2

Reaction notes

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