Ethyl formate → (2S)-2-formylamino-propionic acid tert-butyl ester

HRID 419684Notes

Reaction equation

HRID 419684 reaction equation
Cl.[C:2]([O:6][C:7](=[O:11])[C@H:8]([CH3:10])[NH2:9])([CH3:5])([CH3:4])[CH3:3].C(N(C(C)C)CC)(C)C.[CH:21](OCC)=[O:22]>C(Cl)Cl>[C:2]([O:6][C:7](=[O:11])[C@@H:8]([NH:9][CH:21]=[O:22])[CH3:10])([CH3:5])([CH3:4])[CH3:3]

Participants

5

Reactant 3

HCID 8025Ethyl formateHCID 81531DiisopropylethylamineHCID 11275390tert-Butyl alaninate hydrochloride

Product 1

HCID 79006784(2S)-2-formylamino-propionic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of (2S) alanine tert-butyl ester hydrochloride (3.63 g, 20 mmol) in a mixture of ethyl formate (10 mL) and DCM (5 mL) was added diisopropylethylamine (3.83 mL, 22 mmol) and the reaction mixture was refluxed overnight. The solvents were evaporated and the residue was then triturated in Et2O and filtrated. The filtrates were evaporated and the residue was filtered through a short pad of silica using ethyl acetate as eluent. Evaporation of the solvent afforded the sub-title compound as a colorless oil which crystallised upon standing (2.806 g, 81%): 1H NMR (400 MHz CDCl3) δ 1.43 (3H, d), 1.50 (9H, s), 4.55 (1H, m), 6.31 (1H, br s), 8.16 (1H, s).

Workup

  1. temperaturethe reaction mixture was refluxed overnight
  2. customThe solvents were evaporated
  3. customthe residue was then triturated in Et2O
  4. filtrationfiltrated
  5. customThe filtrates were evaporated
  6. filtrationthe residue was filtered through a short pad of silica
  7. customEvaporation of the solvent

Sources & evidence

ORD record
ord-8295fef46c9f472da882c6aaf01061a7
Source dataset
uspto-grants-2012_01
Patent number
US08093392B2

Reaction notes

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