Acetic Anhydride → HCID 322651, compound

HRID 1907060Notes

Reaction equation

HRID 1907060 reaction equation
[NH2:1][C@H:2]([C:8]([OH:10])=O)[CH2:3][CH2:4][C:5]([OH:7])=O.[C:11](OC(=O)C)(=[O:13])[CH3:12].[OH-].[K+].[CH2:20](N(CC)CC)C>>[C:11]([N:1]1[CH:2]([C:8](=[O:10])[CH3:20])[CH2:3][CH2:4][C:5]1=[O:7])(=[O:13])[CH3:12]

Participants

5

Reactant 4

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 14797Potassium HydroxideHCID 33032L-Glutamic Acid

Product 1

HCID 322651HCID 322651, compound

Conditions

Temperature
60 °C

Procedure

A 500-mL round bottom flask under argon atmosphere is charged with L-glutamic acid 4 (21 g, 0.143 mol), a catalytic amount of N,N-dimethylaminopyridine (150 mg, 1×10−3 mol), acetic anhydride (75 mL) and triethylamine previously distilled over KOH (75 mL). The reaction mixture is maintained at 60° C. for 16 hours. The progression of the reaction is followed by TLC (eluent: ethyl acetate/petroleum ether at a ratio of 8/2). The crude reaction product is concentrated under reduced pressure (rotary evaporator and vane pump) and then taken up in 200 mL of dichloromethane; the organic layer is then washed five times with 100 mL of deionized water and then treated over animal carbon. The product obtained after evaporation of the solvent is purified by crystallization from petroleum ether/CH2Cl2. The crystals are rinsed with petroleum ether.

Workup

  1. customThe crude reaction product
  2. concentrationis concentrated under reduced pressure (rotary evaporator and vane pump)
  3. washthe organic layer is then washed five times with 100 mL of deionized water
  4. additiontreated over animal carbon
  5. customThe product obtained
  6. customafter evaporation of the solvent
  7. customis purified by crystallization from petroleum ether/CH2Cl2
  8. washThe crystals are rinsed with petroleum ether

Sources & evidence

ORD record
ord-699c755f0bcd49e6a5a52772460cd458
Source dataset
uspto-grants-2013_12
Patent number
US08597706B2

Reaction notes

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