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

HRID 1353034Notes

Reaction equation

HRID 1353034 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-Nitrobenzenesulphonyl chloride (9.9 g) was added at 0° C. to a solution of ethyl 3-allyloxycarbonylamino-3-(3-aminophenyl)-propionate from II.1d (10.9 g) in 100 ml of pyridine. After a reaction time of 2 h at 0° C., the mixture was concentrated, treated with 1 N HCl (150 ml) and extracted with dichloromethane. After drying (MgSO4), the solvent was removed, and 16.8 g of product were obtained.

Workup

  1. concentrationAfter a reaction time of 2 h at 0° C., the mixture was concentrated
  2. additiontreated with 1 N HCl (150 ml)
  3. extractionextracted with dichloromethane
  4. dry with materialAfter drying (MgSO4)
  5. customthe solvent was removed

Sources & evidence

ORD record
ord-c6326585e73746ac8f977842e2fc7b96
Source dataset
uspto-grants-2007_05
Patent number
US07220824B1

Reaction notes

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