Methyl formate → Glycine, N-formyl-, ethyl ester

HRID 1507893Notes

Reaction equation

HRID 1507893 reaction equation
Cl.[CH2:2]([O:4][C:5](=[O:8])[CH2:6][NH2:7])[CH3:3].[CH:9](OC)=[O:10]>C(N(CC)CC)C>[CH:9]([NH:7][CH2:6][C:5]([O:4][CH2:2][CH3:3])=[O:8])=[O:10]

Participants

4

Reactant 2

HCID 7865Methyl formateHCID 2723640Glycine ethyl ester, hydrochloride

Product 1

HCID 76615Glycine, N-formyl-, ethyl esterYield 93%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

To a 5 L three neck round bottom flask equipped with a mechanic stirrer, a pressure-equalizing funnel and a condenser bearing a calcium chloride drying tube was added glycine ethyl ester hydrochloride (500 g, 3.583 mol) and methyl formate (1.8 L). The suspension was brought to reflux and triethylamine (556 mL) was added to the reaction. The reaction was stirred and refluxed overnight. The reaction was cooled to room temperature and filtered through a Buchner funnel to remove triethylamine hydrochloride salt. The filtrate was concentrated and dried over high vacuum to yield 320 g (93%) of the title compound.

Workup

  1. temperatureto reflux
  2. temperaturerefluxed overnight
  3. filtrationfiltered through a Buchner funnel
  4. customto remove triethylamine hydrochloride salt
  5. concentrationThe filtrate was concentrated
  6. customdried over high vacuum

Sources & evidence

ORD record
ord-86ca9c2bd827434496c8f5f36fcebcd3
Source dataset
uspto-grants-2015_12
Patent number
US09221826B2

Reaction notes

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