Triethylamine → HCID 86024925, compound

HRID 917617Notes

Reaction equation

HRID 917617 reaction equation
[CH3:1][O:2][C:3](=[O:12])[CH2:4][C:5](=[O:11])[CH2:6][C:7]([O:9][CH3:10])=[O:8].C(N(CC)CC)C.C(NC1C=CC(S([N:33]=[N+:34]=[N-])(=O)=O)=CC=1)(=O)C>C(#N)C>[CH3:10][O:9][C:7](=[O:8])[C:6](=[N+:33]=[N-:34])[C:5](=[O:11])[CH2:4][C:3]([O:2][CH3:1])=[O:12]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 74591Dimethyl 3-oxoglutarateHCID 51291854-Acetamidobenzenesulfonyl azide

Product 1

HCID 86024925HCID 86024925, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a mixture of 3-ketoglutaric acid dimethyl ester 15.0 g, triethylamine 9.6 g and acetonitrile 300 ml is portionwise added 4-acetylaminobenzensulfonylazide 20.7 g at 0° C. The mixture is stirred at room temperature for 30 minutes. After removal of the precipitate by filtration the filtrate is concentrated in vacuo. The residue is diluted with a mixture of hexane and diethyl ether (1:1). The insoluble materials are removed by filtration and the filtrate is concentrated in vacuo. The residue is purified with column chromatography (silica gel 225 g, solvent; hexane:ethyl acetate=5:13:1) to give 2-diazo-3-ketoglutaric acid dimethyl ester as a pale yellow oil, 16.03 g.

Workup

  1. customat 0° C
  2. customAfter removal of the precipitate
  3. filtrationby filtration the filtrate
  4. concentrationis concentrated in vacuo
  5. additionThe residue is diluted with a mixture of hexane and diethyl ether (1:1)
  6. customThe insoluble materials are removed by filtration
  7. concentrationthe filtrate is concentrated in vacuo
  8. customThe residue is purified with column chromatography (silica gel 225 g, solvent; hexane:ethyl acetate=5:13:1)

Sources & evidence

ORD record
ord-ae1f873b26ae4713ba409213d1a62320
Source dataset
uspto-grants-2007_09
Patent number
US07273868B2

Reaction notes

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