Acetic Acid → HCID 54067448, compound

HRID 363436Notes

Reaction equation

HRID 363436 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

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 IN 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 IN 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-8d7a1e0b294a4d119a2fe55b0d3d09de
Source dataset
uspto-grants-1999_02
Patent number
US05874448

Reaction notes

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