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

HRID 1840622Notes

Reaction equation

HRID 1840622 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 carried out analogously 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 at 0° C. 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. The reaction solution was allowed to warm to room temperature, stirred overnight at room temperature and then washed twice with saturated NaCl solution. The phases were separated and the organic phase was dried over magnesium sulfate. After filtration and removal of the solvent in vacuo, the residue obtained 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. filtrationAfter filtration and removal of the solvent in vacuo
  6. customthe residue obtained
  7. distillationwas distilled in vacuo

Sources & evidence

ORD record
ord-ddbfc61afadb44a1be267c8ec9f2d04f
Source dataset
uspto-grants-2004_01
Patent number
US06680333B2

Reaction notes

Loading…