Benzenesulfonyl chloride → Ethyl 3-benzenesulfonamidopropanoate

HRID 2384069Notes

Reaction equation

HRID 2384069 reaction equation
[C:1]1([S:7](Cl)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:11]([O:13][C:14](=[O:18])[CH2:15][CH2:16][NH2:17])[CH3:12].C(OCC)(=O)C>N1C=CC=CC=1>[CH2:11]([O:13][C:14](=[O:18])[CH2:15][CH2:16][NH:17][S:7]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)(=[O:9])=[O:8])[CH3:12]

Participants

5

Reactant 3

HCID 7369Benzenesulfonyl chlorideHCID 8857Ethyl AcetateHCID 419889Ethyl 3-aminopropanoate

Product 1

HCID 3795547Ethyl 3-benzenesulfonamidopropanoate

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of benzenesulfonyl chloride (500 mg, 2.83 mmol) in pyridine (10 mL) is added 3-amino-propionic acid ethyl ester (672 mg, 8.49 mmol) and the mixture is stirred at room temperature for 18 hours. The mixture is poured into ethyl acetate and is washed with aqueous 1M HCl and brine. The organic phase is dried over magnesium sulfate and the solvent is removed under reduced pressure. The residue is purified by column chromatography using a gradient of 10-50% heptane/EtOAc to afford 3-benzenesulfonylaminopropionic acid ethyl ester. MS 258.3 (M+1); 1H-NMR (400 MHz, CDCl3); δ ppm 1.24 (t, 3H), 2.53 (t, 2H), 3.21 (q, 2H), 5.22 (m, 1H), 7.51-7.61 (m, 3H), 7.87 (d, J=7.20 Hz, 2H).

Workup

  1. washis washed with aqueous 1M HCl and brine
  2. dry with materialThe organic phase is dried over magnesium sulfate
  3. customthe solvent is removed under reduced pressure
  4. customThe residue is purified by column chromatography

Sources & evidence

ORD record
ord-aa91a0ae05ba456dbee4bec79c5bea52
Source dataset
uspto-grants-2012_09
Patent number
US08263629B2

Reaction notes

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