Triethylamine → 3-(3-Methoxy-benzenesulfonylamino)-propionic acid ethyl ester

HRID 1700173Notes

Reaction equation

HRID 1700173 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([S:9](Cl)(=[O:11])=[O:10])[CH:6]=[CH:7][CH:8]=1.C(N(CC)CC)C.Cl.[CH2:21]([O:23][C:24](=[O:28])[CH2:25][CH2:26][NH2:27])[CH3:22]>CC(C)=O>[CH2:21]([O:23][C:24](=[O:28])[CH2:25][CH2:26][NH:27][S:9]([C:5]1[CH:6]=[CH:7][CH:8]=[C:3]([O:2][CH3:1])[CH:4]=1)(=[O:11])=[O:10])[CH3:22]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 458475beta-Alanine, ethyl ester, hydrochlorideHCID 27375043-Methoxybenzenesulfonyl chloride

Product 1

HCID 700249813-(3-Methoxy-benzenesulfonylamino)-propionic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 3-methoxybenzenesulfonyl chloride (3.53 g, 12.1 mmol) and triethylamine (3.45 g, 17.1 mmol) in acetone at 0° C. was added β-alanine ethyl ester hydrochloride (2.00 g, 17.1 mmol) under a nitrogen atmosphere. After 4 days, the reaction was concentrated in vacuo. The residue was partitioned between 0.1 N HCl solution and EtOAc, the organic layer separated, washed with brine, dried (Na2SO4), and concentrated in vacuo to provide the crude product which was used without further purification.

Workup

  1. concentrationthe reaction was concentrated in vacuo
  2. customThe residue was partitioned between 0.1 N HCl solution and EtOAc
  3. customthe organic layer separated
  4. washwashed with brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-65f4b4174c934b17aee7a0d7d88a68bc
Source dataset
uspto-grants-2002_02
Patent number
US06350755B1

Reaction notes

Loading…