Acetic Anhydride → HCID 322651, compound

HRID 979550Notes

Reaction equation

HRID 979550 reaction equation
[NH2:1][C@H:2]([C:8]([OH:10])=O)[CH2:3][CH2:4][C:5]([OH:7])=O.[CH2:11](N(CC)CC)C.[C:18](OC(=O)C)(=[O:20])[CH3:19]>CN(C)C1C=CN=CC=1>[C:18]([N:1]1[CH:2]([C:8](=[O:10])[CH3:11])[CH2:3][CH2:4][C:5]1=[O:7])(=[O:20])[CH3:19]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 33032L-Glutamic Acid

Product 1

HCID 322651HCID 322651, compound

Reagents, catalysts & solvents 1

HCID 142844-(Dimethylamino)pyridineCatalyst

Procedure

Following the method of W. Steglich, et al., Liebigs, Ann. Chem., 1753, 1974, (21.0 gm) of glutamic acid in 75 ml of acetic anhydride, 150 mg of 4-dimethylamino-pyridine, and 75 ml of triethylamine was heated 60° C. overnight. The reaction mixture was then concentrated in vacuo, the residue taken up in dichloromethane and washed with water. The organic portion was treated with charcoal, filtered, concentrated and 1,5-diacetyl-2-pyrroidone was obtained crystalline from ether-dichloromethane, mp 62° C. 'H NMR (δ CDCl3): 1.8-2.8 (m, CH2), 2.3 (s, 3H, CH3), 2.55 (s, 3H, CH3), 4.8-5.0 ppm (dd, 1H, CHN).

Workup

  1. concentrationThe reaction mixture was then concentrated in vacuo
  2. washwashed with water
  3. additionThe organic portion was treated with charcoal
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-75e01e1a7ac24c17a3425baf5a031706
Source dataset
uspto-grants-1987_05
Patent number
US04668703

Reaction notes

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