Succinic anhydride → N-(3-Carboxypropanoyl)-N-methyl-glycine Benzyl Ester

HRID 377768

Reaction equation

HRID 377768 reaction equation
[CH2:1]([O:8][C:9](=[O:13])[CH2:10][NH:11][CH3:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:14]1(=[O:20])[O:19][C:17](=[O:18])[CH2:16][CH2:15]1>C1(C)C=CC=CC=1>[CH2:1]([O:8][C:9](=[O:13])[CH2:10][N:11]([C:14](=[O:20])[CH2:15][CH2:16][C:17]([OH:19])=[O:18])[CH3:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 7922Succinic anhydrideHCID 7019103Benzyl 2-(methylamino)acetate

Product 1

HCID 19356295N-(3-Carboxypropanoyl)-N-methyl-glycine Benzyl EsterYield 86.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of sarcosine benzyl ester (3.0 g, 30.7 mmol) and succinic anhydride (5.5 g, 30.7 mmol) in toluene (75 mL) was heated to reflux for 3 h, cooled, filtered, and the filtrate was concentrated. The residue was taken up in 5% aqueous sodium carbonate and extracted with ethyl acetate. The aqueous phase was adjusted to pH 3 with concentrated hydrochloric using Congo Red paper and extracted with ethyl acetate. The organic phase was washed with water, dried (magnesium sulfate) and concentrated to yield the title compound (7.4 g, 67.5%): TLC Rf 0.48 (silica, 9:1:1 dichloromethane:methanol:formic acid).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 3 h
  3. temperaturecooled
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated
  6. extractionextracted with ethyl acetate
  7. concentrationwith concentrated hydrochloric
  8. extractionextracted with ethyl acetate
  9. washThe organic phase was washed with water
  10. dry with materialdried (magnesium sulfate)
  11. concentrationconcentrated

Sources & evidence

ORD record
ord-0ea382043e6642be93dc1fb60719a963
Source dataset
uspto-grants-2000_02
Patent number
US06028087

Linked notes

Loading…