Glycine methyl ester hydrochloride → HCID 19801628, compound

HRID 1646178Notes

Reaction equation

HRID 1646178 reaction equation
Cl.[CH3:2][O:3][C:4](=[O:7])[CH2:5][NH2:6].Br[CH2:9][CH:10]=[CH:11][CH2:12][P:13](=[O:20])([O:17][CH2:18][CH3:19])[O:14][CH2:15][CH3:16]>CO.C(N(CC)CC)C>[CH2:18]([O:17][P:13]([O:14][CH2:15][CH3:16])([CH2:12]/[CH:11]=[CH:10]/[CH2:9][NH:6][CH2:5][C:4]([O:3][CH3:2])=[O:7])=[O:20])[CH3:19]

Participants

5

Reactant 2

HCID 122755Glycine methyl ester hydrochlorideHCID 54254531HCID 54254531, compound

Product 1

HCID 19801628HCID 19801628, compoundYield 34%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8471TriethylamineSolvent

Procedure

A solution of glycine methyl ester hydrochloride (1.6 g, 12.7 mmol) and diethyl (4-bromo-2-butenyl)phosphonate (Example E) (3.14 g, 11.6 mmol) in methanol and triethylamine (5 ml) is heated at reflux for 16 hours. The solvent is removed in vacuo and the residue dissolved in water and extracted with chloroform (2×70 ml). The organic layer is dried over magnesium sulfate, filtered and evaporated. The residue is purified over silica gel (0-2.5% methanol in chloroform as eluant) to give 1.1 g of a clear oil.

Workup

  1. temperatureat reflux for 16 hours
  2. customThe solvent is removed in vacuo
  3. dissolutionthe residue dissolved in water
  4. extractionextracted with chloroform (2×70 ml)
  5. dry with materialThe organic layer is dried over magnesium sulfate
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue is purified over silica gel (0-2.5% methanol in chloroform as eluant)

Sources & evidence

ORD record
ord-f23ca0bb2a1041e880d2bc0b19cf26bf
Source dataset
uspto-grants-1993_01
Patent number
US05179085

Reaction notes

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