Triethylamine → n-Formyl-l-leucine tert-butyl ester

HRID 1007569

Reaction equation

HRID 1007569 reaction equation
C(N(CC)CC)C.Cl.[C:9]([O:13][C:14](=[O:21])[C@H:15]([CH2:17][CH:18]([CH3:20])[CH3:19])[NH2:16])([CH3:12])([CH3:11])[CH3:10].[CH:22](OCC#N)=[O:23]>ClCCl>[C:9]([O:13][C:14](=[O:21])[C@H:15]([CH2:17][CH:18]([CH3:19])[CH3:20])[NH:16][CH:22]=[O:23])([CH3:12])([CH3:11])[CH3:10]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 4205685(Formyloxy)acetonitrileHCID 12451443tert-butyl (2S)-2-amino-4-methylpentanoate hydrochloride

Product 1

HCID 11160222n-Formyl-l-leucine tert-butyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

The preparation was performed in analogy to W. Duczek et al., Synthesis, 37-38 (1996). A solution of 4.04 g (40 mmol) of triethylamine in 10 mL of dichloromethane was added to a solution of 8.94 g (40 mmol) of L-leucine tert-butyl ester hydrochloride and 3.4 g (40 mmol) of cyanomethyl formate in 60 mL of dichloromethane at 0° C. The reaction solution was allowed to warm to room temperature, stirred at room temperature overnight, and then washed twice with saturated NaCl solution. The phases were separated and the organic phase was dried over magnesium sulfate. The residue obtained after filtration and removal of the solvent in vacuo was distilled in vacuo. Yield: 7.5 g (87%). Boiling point: 118° C./2.7 Pa (0.02 torr).

Workup

  1. customDuczek et al., Synthesis, 37-38 (1996)
  2. washwashed twice with saturated NaCl solution
  3. customThe phases were separated
  4. dry with materialthe organic phase was dried over magnesium sulfate
  5. customThe residue obtained
  6. filtrationafter filtration and removal of the solvent in vacuo
  7. distillationwas distilled in vacuo

Sources & evidence

ORD record
ord-9e9028be0e544e89848222ce1c80d7fa
Source dataset
uspto-grants-2004_09
Patent number
US06794517B2

Linked notes

Loading…