Ethyl formate → 5-(N-formylamino)-valeric acid ethyl ester

HRID 414737Notes

Reaction equation

HRID 414737 reaction equation
C(N(CC)CC)C.Cl.[CH2:9]([O:11][C:12](=[O:18])[CH2:13][CH2:14][CH2:15][CH2:16][NH2:17])[CH3:10].[CH2:19]([O:21]C=O)C>>[CH2:9]([O:11][C:12](=[O:18])[CH2:13][CH2:14][CH2:15][CH2:16][NH:17][CH:19]=[O:21])[CH3:10]

Participants

4

Reactant 3

HCID 8025Ethyl formateHCID 8471TriethylamineHCID 16094861Ethyl 5-aminopentanoate hydrochloride

Product 1

HCID 542728725-(N-formylamino)-valeric acid ethyl ester

Procedure

1.4 ml of triethylamine are added to 1.8 g of 5-aminovaleric acid ethyl ester hydrochloride in 40 ml of formic acid ethyl ester and the whole is then heated under reflux for 2 hours. The precipitate is filtered off, washed with a small quantity of formic acid ethyl ester and concentrated by evaporation under reduced pressure in a rotary evaporator. The residue is partitioned between methylene chloride and sodium bicarbonate solution, and the organic phase is then washed with brine, dried and concentrated by evaporation. The title compound is obtained in the form of an oil.

Workup

  1. temperaturethe whole is then heated
  2. temperatureunder reflux for 2 hours
  3. filtrationThe precipitate is filtered off
  4. washwashed with a small quantity of formic acid ethyl ester
  5. concentrationconcentrated by evaporation under reduced pressure in a rotary evaporator
  6. customThe residue is partitioned between methylene chloride and sodium bicarbonate solution
  7. washthe organic phase is then washed with brine
  8. customdried
  9. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-1ec757bc98004f3490119112f063295b
Source dataset
uspto-grants-1988_12
Patent number
US04794109

Reaction notes

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