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

HRID 1060882Notes

Reaction equation

HRID 1060882 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 3-amino propionic acid 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-46d05f99166b474a854569f46630920d
Source dataset
uspto-grants-2003_02
Patent number
US06525074B2

Reaction notes

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