Acetic Acid → HCID 54067448, compound

HRID 618697Notes

Reaction equation

HRID 618697 reaction equation
[CH3:1][O:2][C:3](=[O:12])[C@H:4]([CH2:6][CH2:7][C:8]([O:10][CH3:11])=[O:9])[NH2:5].[N:13](OCCC(C)C)=O.C(O)(=O)C>C1C=CC=CC=1>[N+:5](=[C:4]([CH2:6][CH2:7][C:8]([O:10][CH3:11])=[O:9])[C:3]([O:2][CH3:1])=[O:12])=[N-:13]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 8053Isoamyl NitriteHCID 93032Dimethyl glutamate

Product 1

HCID 54067448HCID 54067448, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

Part A. A solution of L-glutamic acid dimethyl ester (2.6 g, 14.8 mmol), isoamyl nitrite (2.13 mL, 15.9 mmol) and acetic acid (0.22 mL) in benzene (150 mL) is heated to reflux for one hour. The solution is washed with 1N aqueous sulfuric acid, water, saturated sodium hydrogen carbonate solution, water and brine (50 mL each). The solvent is removed in vacuo to yield dimethyl 2-diazopentane-1,5-dioate which can be further purified by column chromatography.

Workup

  1. temperatureto reflux for one hour
  2. washThe solution is washed with 1N aqueous sulfuric acid, water, saturated sodium hydrogen carbonate solution, water and brine (50 mL each)
  3. customThe solvent is removed in vacuo

Sources & evidence

ORD record
ord-5a464acd05374937bce0428dce020be6
Source dataset
uspto-grants-1999_09
Patent number
US05955476

Reaction notes

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