Methyl propiolate → CGP-47292 methyl ester

HRID 218814Notes

Reaction equation

HRID 218814 reaction equation
[F:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]([F:12])[C:3]=1[CH2:4][N:5]=[N+:6]=[N-:7].[C:13]([O:17][CH3:18])(=[O:16])[C:14]#[CH:15].O=C1O[C@H]([C@H](CO)O)C(O)=C1O>C(O)C>[F:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]([F:12])[C:3]=1[CH2:4][N:5]1[CH:15]=[C:14]([C:13]([O:17][CH3:18])=[O:16])[N:7]=[N:6]1

Participants

5

Reactant 3

HCID 13536Methyl propiolateHCID 108883232-(Azidomethyl)-1,3-difluorobenzeneHCID 54670067L-Ascorbic Acid

Product 1

HCID 22716778CGP-47292 methyl esterYield 94%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2,6-Difluorobenzyl azide (3.0 g, 17.7 mmoles) is suspended in ethanol (30 ml), then methyl propiolate (IV) (1.6 g, 19.6 mmoles), ascorbic acid (317 mg, 1.8 mmoles) and CuSO4 pentahydrate (50 mg, 0.18 mmole) are added. The reaction mixture is kept at 25° C. under stirring overnight. The mixture is concentrated, taken up with ethyl acetate and washed with an ammonia diluted solution. The organic phase is dried, filtered, concentrated under reduced pressure. A crystalline white solid is obtained in 94% yield.

Workup

  1. customis kept at 25° C.
  2. concentrationThe mixture is concentrated
  3. washwashed with an ammonia diluted solution
  4. customThe organic phase is dried
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customA crystalline white solid is obtained in 94% yield

Sources & evidence

ORD record
ord-2d85bcc220de497183730ab18b4bb4bb
Source dataset
uspto-grants-2012_06
Patent number
US08198459B2

Reaction notes

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