Methanol → Ethyl N-(methoxycarbonyl)glycinate

HRID 2412318Notes

Reaction equation

HRID 2412318 reaction equation
[C:1](Cl)(Cl)=[O:2].Cl.[CH2:6]([O:8][C:9](=[O:12])[CH2:10][NH2:11])[CH3:7].C(N(CC)CC)C.[CH3:20][OH:21]>C1(C)C=CC=CC=1>[CH2:6]([O:8][C:9](=[O:12])[CH2:10][NH:11][C:20]([O:2][CH3:1])=[O:21])[CH3:7]

Participants

6

Reactant 4

HCID 887MethanolHCID 6371PhosgeneHCID 8471TriethylamineHCID 2723640Glycine ethyl ester, hydrochloride

Product 1

HCID 235150Ethyl N-(methoxycarbonyl)glycinate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of phosgene (70.4 g, 0.71 mole) in dry toluene (300 ml), a mixture of glycine ethyl ester hydrochloride (99.1 g, 0.71 mole) and triethylamine (158 g, 1.56 mole) was slowly added at 0° C. The reaction was exothermic. After 2 hrs. of stirring, anhydrous methanol was added to the reaction mixture and stirring was continued for another 0.5 hrs. The reaction mixture was partitioned between water and chloroform, then the pH of the solution was adjusted to 4 with concentrated HCl. The chloroform layer was dried and the solvent was evaporated to obtain the N-carbomethoxy glycine ethyl ester with the structure being confirmed by spectroscopy.

Workup

  1. additionwas slowly added at 0° C
  2. stirringstirring
  3. waitwas continued for another 0.5 hrs
  4. customThe reaction mixture was partitioned between water and chloroform
  5. dry with materialThe chloroform layer was dried
  6. customthe solvent was evaporated

Sources & evidence

ORD record
ord-73735598e42c4e7f8adaa63b7cb6d57c
Source dataset
uspto-grants-1985_01
Patent number
US04491548

Reaction notes

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