Benzenesulfonyl chloride → Ethyl 3-benzenesulphonylamino3-(3-nitrophenyl)-propionate

HRID 1596559Notes

Reaction equation

HRID 1596559 reaction equation
[C:1]1([S:7](Cl)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.[NH2:12][CH:13]([C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([N+:26]([O-:28])=[O:27])[CH:21]=1)[CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16].C(N(CC)CC)C>N1C=CC=CC=1>[C:1]1([S:7]([NH:12][CH:13]([C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([N+:26]([O-:28])=[O:27])[CH:21]=2)[CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 7369Benzenesulfonyl chlorideHCID 8471TriethylamineHCID 16188861Ethyl 3-amino-3-(3-nitrophenyl)propanoate hydrochloride

Product 1

HCID 11188106Ethyl 3-benzenesulphonylamino3-(3-nitrophenyl)-propionateYield 82.8%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

8.1 g of phenylsulphonyl chloride were added at 0° C. to a solution of 10 g of (1b) in 100 ml of pyridine. After a reaction time of 15 min, 6.3 ml of triethylamine were added and the mixture was stirred at room temperature. After 5 h, it was concentrated, treated with 1 N HCl, extracted with dichloromethane, dried over MgSO4 and concentrated. Chromatographic purification (dichloromethane/methanol=5:1) yielded 11.4 g of a white solid.

Workup

  1. concentrationit was concentrated
  2. additiontreated with 1 N HCl
  3. extractionextracted with dichloromethane
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. customChromatographic purification (dichloromethane/methanol=5:1)

Sources & evidence

ORD record
ord-78116723c0344e6387232f51427346a5
Source dataset
uspto-grants-2001_09
Patent number
US06291503B1

Reaction notes

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