Acetic Anhydride → N-Formyl-p-methoxyphenylglycine methyl ester

HRID 37462Notes

Reaction equation

HRID 37462 reaction equation
[CH3:1][O:2][C:3](=[O:21])[CH2:4][N:5]([C:13]1[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=1)[C:6](OC(C)(C)C)=[O:7].C(OC(=O)C)(=O)C>C(O)=O>[CH3:1][O:2][C:3](=[O:21])[CH2:4][N:5]([C:13]1[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=1)[CH:6]=[O:7]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 18469309N-Boc-p-methoxyphenylglycine methyl ester

Product 1

HCID 19935601N-Formyl-p-methoxyphenylglycine methyl ester

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

In 250 ml of formic acid was dissolved 36.9 g of N-Boc-p-methoxyphenylglycine methyl ester, and the mixture was stirred at room temperature for 3 hours and subsequently at 40°-50° C. for 1 hour. After dropwise addition of 24.8 ml (2.1 eq.) of acetic anhydride, the mixture was stirred at room temperature overnight and 40°-50° C. for 2 hours. After the solvent was distilled off, the residue was neutralized with an aqueous solution of sodium hydrogencarbonate, followed by extraction with ethyl acetate. The organic layer was washed with water and a saturated aqueous solution of sodium chloride and dried over magnesium sulfate. The solvent was distilled off. The crystals were collected by filtration with hexane.

Workup

  1. stirringthe mixture was stirred at room temperature overnight and 40°-50° C. for 2 hours
  2. distillationAfter the solvent was distilled off
  3. extractionfollowed by extraction with ethyl acetate
  4. washThe organic layer was washed with water
  5. dry with materiala saturated aqueous solution of sodium chloride and dried over magnesium sulfate
  6. distillationThe solvent was distilled off
  7. filtrationThe crystals were collected by filtration with hexane

Sources & evidence

ORD record
ord-c9643de5a4b04cb2a9a78d3775d719f2
Source dataset
uspto-grants-1995_05
Patent number
US05420275

Reaction notes

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