Acetic Anhydride → Glycine, N-formyl-, ethyl ester

HRID 1728959Notes

Reaction equation

HRID 1728959 reaction equation
[CH:1]([O-])=[O:2].[Na+].Cl.[CH2:6]([O:8][C:9](=[O:12])[CH2:10][NH2:11])[CH3:7].C(OC(=O)C)(=O)C>C(O)=O>[CH2:6]([O:8][C:9](=[O:12])[CH2:10][NH:11][CH:1]=[O:2])[CH3:7]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 2723640Glycine ethyl ester, hydrochlorideHCID 2723810Sodium Formate

Product 1

HCID 76615Glycine, N-formyl-, ethyl esterYield 85%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent2×

Procedure

A hot solution of sodium formate (150 g) in formic acid (200 mL) was added to a hot solution of glycine ethyl ester hydrochloride (228.7 g; 1.64 mol) in hot formic acid (250 mL). This was allowed to stir at room temperature for 1 hour. Small portions of acetic anhydride (450 g) were added to the well-stirred suspension as an exothermic reaction ensued. The suspension was stirred overnight, the solid was filtered and the filtrate was distilled in vacuo to remove excess reagents. The residue was filtered and then distilled to give N-formylglycine ethyl ester (182 g; 85%) having a boiling point of 105°-110° C. under vacuum.

Workup

  1. stirringThe suspension was stirred overnight
  2. filtrationthe solid was filtered
  3. distillationthe filtrate was distilled in vacuo
  4. customto remove excess reagents
  5. filtrationThe residue was filtered
  6. distillationdistilled

Sources & evidence

ORD record
ord-f73e79a502bd4aa98922a7d8f907e566
Source dataset
uspto-grants-1994_07
Patent number
US05329012

Reaction notes

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