Propargyl bromide → HCID 70025903, compound

HRID 1355611Notes

Reaction equation

HRID 1355611 reaction equation
CC[O-].[Na+].[Na].[C:6]1([CH2:12][O:13][C:14]([NH:16][CH:17]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[C:18]([O:20][CH2:21][CH3:22])=[O:19])=[O:15])[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[CH2:28](Br)[C:29]#[CH:30]>C(O)C.C1(C)C=CC=CC=1>[C:6]1([CH2:12][O:13][C:14]([NH:16][C:17]([C:28]#[C:29][CH3:30])([C:18]([O:20][CH2:21][CH3:22])=[O:19])[C:23]([O:25][CH2:26][CH3:27])=[O:24])=[O:15])[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

7

Reactant 4

HCID 7842Propargyl bromideHCID 259787Diethyl 2-(benzyloxycarbonylamino)malonateHCID 2723922Sodium ethoxideHCID 5360545Sodium

Product 1

HCID 70025903HCID 70025903, compoundYield 41.9%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 1140TolueneSolvent

Procedure

A solution of sodium ethylate previously prepared from 500 mg of sodium in 20 ml of ethanol is added to 6 g of diethyl 2-[[(phenylmethoxy)carbonyl]amino]-propanedioate (prepared according to Bladon. C. M. J.Chem. Soc. Perkin. Trans I 9, 1151-1158 (1990) in 30 ml of ethanol then, after 30 minutes, 3 g of propargyl bromide at 80% in toluene is added and the reaction mixture is heated under reflux for 1 hour. The reaction mixture is then brought back to ambient temperature followed by evaporation under reduced pressure, taking up in dichloromethane, washing and drying. After evaporation under reduced pressure 6 g of the expected product is obtained which is purified by chromatography, eluting with a Cyclohexane/Ethyl acetate mixture 85/15. 2.82 g of purified product is obtained.

Workup

  1. customprepared
  2. temperaturethe reaction mixture is heated
  3. temperatureunder reflux for 1 hour
  4. customis then brought back to ambient temperature
  5. customfollowed by evaporation under reduced pressure
  6. washwashing
  7. customdrying
  8. customAfter evaporation under reduced pressure 6 g of the expected product
  9. customis obtained which
  10. customis purified by chromatography
  11. washeluting with a Cyclohexane/Ethyl acetate mixture 85/15

Sources & evidence

ORD record
ord-7f450d5c6e954ce29e6f4183f2a9446a
Source dataset
uspto-grants-2003_07
Patent number
US06586442B2

Reaction notes

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