Water → HCID 21242406, compound

HRID 1761725Notes

Reaction equation

HRID 1761725 reaction equation
[CH3:1][O:2][C:3]([NH:5][CH2:6][C:7]([O:9][CH2:10][CH3:11])=[O:8])=[O:4].[H-].[Na+].[CH2:14](Br)[C:15]#[CH:16].O>CN(C)C=O>[CH2:16]([N:5]([C:3]([O:2][CH3:1])=[O:4])[CH2:6][C:7]([O:9][CH2:10][CH3:11])=[O:8])[C:15]#[CH:14]

Participants

6

Reactant 4

HCID 962WaterHCID 7842Propargyl bromideHCID 24758Sodium hydrideHCID 235150Ethyl N-(methoxycarbonyl)glycinate

Product 1

HCID 21242406HCID 21242406, compoundYield 64.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

100 g of ethyl N-methoxycarbonylglycinate were dissolved in 600 ml of N,N-dimethylformamide. Then ice-cooling the mixture, 25 g of sodium hydride (60% oil dispersion) were added thereto under a nitrogen atmosphere. After the reaction mixture was stirred for 2 hours, 81.3 g of propargyl bromide were dropped thereto over 2 hours. After the mixture was further stirred for an hour, the reaction product was poured into water and the aqueous layer was washed with hexane. Then it was subjected to three times of extraction with 100 ml of ether. The ether layers were combined together and dried over anhydrous magnesium sulfate and the solvent was evaporated off to obtain 79.8 g of ethyl N-propargyl-N-methoxycarbonylglycinate.

Workup

  1. additionwere added
  2. waitover 2 hours
  3. stirringAfter the mixture was further stirred for an hour
  4. washthe aqueous layer was washed with hexane
  5. extractionThen it was subjected to three times of extraction with 100 ml of ether
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customthe solvent was evaporated off

Sources & evidence

ORD record
ord-dbaf1a3adf2a48ecaf5784d95cd1b974
Source dataset
uspto-grants-1989_05
Patent number
US04827020

Reaction notes

Loading…