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

HRID 877656

Reaction equation

HRID 877656 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-a65f2f54fff342d3966946a9c29b79b0
Source dataset
uspto-grants-2015_03
Patent number
US08987268B2

Linked notes

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