Sodium Chloride → HCID 14580243, compound

HRID 1761723Notes

Reaction equation

HRID 1761723 reaction equation
[CH3:1][N:2]([C:7]([O:9][CH3:10])=[O:8])[CH2:3][C:4]([OH:6])=[O:5].[H-].[Na+].[CH2:13](Br)[C:14]#C.[Cl-].[Na+].[CH3:19]N(C)C=O>>[CH2:1]([N:2]([C:7]([O:9][CH3:10])=[O:8])[CH2:3][C:4]([O:6][CH3:19])=[O:5])[C:13]#[CH:14]

Participants

6

Reactant 5

HCID 5234Sodium ChlorideHCID 6228DimethylformamideHCID 7842Propargyl bromideHCID 24758Sodium hydrideHCID 14346035N-(methoxycarbonyl)-N-methylGlycine

Product 1

HCID 14580243HCID 14580243, compound

Procedure

5.0 g of methyl N-methoxycarbonylglycine were dissolved in 30 ml of N,N-dimethylformamide. Then ice-cooling the mixture, 1.5 g of sodium hydride (60% oil dispersion) were added thereto under a nitrogen atmosphere and stirred for 20 minutes. Thereafter 6.0 g of propargyl bromide were dropped thereto over 15 minutes and further stirred for 40 minutes. Then the reaction mixture was poured into ice-water and sodium chloride was added thereto to saturate the same. Then the aqueous layer was washed with hexane and it was subjected to two 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 3.9 g of methyl N-propargyl-N-methoxycarbonylglycinate (nD18 : 1.4891).

Workup

  1. additionwere added
  2. waitover 15 minutes
  3. stirringfurther stirred for 40 minutes
  4. additionwas added
  5. concentrationto saturate the same
  6. washThen the aqueous layer was washed with hexane and it
  7. extractionwas subjected to two times of extraction with 100 ml of ether
  8. dry with materialdried over anhydrous magnesium sulfate
  9. customthe solvent was evaporated off

Sources & evidence

ORD record
ord-ac43e4edb6ac417da16ded1f464dbdd9
Source dataset
uspto-grants-1989_05
Patent number
US04827020

Reaction notes

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