Diethyl Ether → Methyl N-acetyl-beta-alaninate

HRID 1681674Notes

Reaction equation

HRID 1681674 reaction equation
Cl.[CH3:2][O:3][C:4](=[O:8])[CH2:5][CH2:6][NH2:7].[C:9](Cl)(=[O:11])[CH3:10].C(=O)([O-])[O-].[K+].[K+].CCOCC>ClCCl>[CH3:2][O:3][C:4](=[O:8])[CH2:5][CH2:6][NH:7][C:9](=[O:11])[CH3:10]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 6367Acetyl chlorideHCID 11430Potassium Carbonate2×HCID 2734767Methyl 3-aminopropanoate hydrochloride

Product 1

HCID 12859671Methyl N-acetyl-beta-alaninate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A 10.0 g portion of β-alanine methyl ester hydrochloride was slurried in 200 ml of dichloromethane. A 20 ml portion of acetyl chloride and 20 g of anhydrous potassium carbonate were added and the mixture was stirred vigorously for 48 hours. The mixture was poured into 400 ml of ether, 20 g of fresh anhydrous potassium carbonate added and the solids allowed to settle for 15 minutes. Suction filtration through celite and concentration gave an oil. This oil was concentrated four times from 50 ml portions of toluene, giving 4.73 g of the desired compound as a pale yellow oil.

Workup

  1. additionadded
  2. waitto settle for 15 minutes
  3. filtrationSuction filtration
  4. concentrationthrough celite and concentration
  5. customgave an oil
  6. concentrationThis oil was concentrated four times from 50 ml portions of toluene

Sources & evidence

ORD record
ord-fd236b0bb3f645efb5796ee90a6f295d
Source dataset
uspto-grants-1992_12
Patent number
US05173510

Reaction notes

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