(Formyloxy)acetonitrile → (s)-n-Formyl-beta-cyclopropylalanine tert-butyl ester

HRID 1007571

Reaction equation

HRID 1007571 reaction equation
[C:1]([O:5][C:6](=[O:13])[C@H:7]([CH2:9][CH:10]1[CH2:12][CH2:11]1)[NH2:8])([CH3:4])([CH3:3])[CH3:2].[CH:14](OCC#N)=[O:15]>ClCCl>[C:1]([O:5][C:6](=[O:13])[C@H:7]([CH2:9][CH:10]1[CH2:12][CH2:11]1)[NH:8][CH:14]=[O:15])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 4205685(Formyloxy)acetonitrileHCID 12018345(S)-tert-Butyl 2-amino-3-cyclopropylpropanoate

Product 1

HCID 12018346(s)-n-Formyl-beta-cyclopropylalanine tert-butyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 10 g (54 mmol) of (S)-β-cyclopropylalanine tert-butyl ester and 4.7 g (55.2 mmol) of cyanomethyl formate in 100 mL of dichloromethane was stirred at room temperature overnight. The residue obtained after removal of the solvent in vacuo was distilled in vacuo. Yield: 8.8 g (76%). Boiling point 120° C./40 Pa (0.3 torr).

Workup

  1. customThe residue obtained
  2. customafter removal of the solvent in vacuo
  3. distillationwas distilled in vacuo

Sources & evidence

ORD record
ord-fa7a2359d00246fbaccb855bb320c870
Source dataset
uspto-grants-2004_09
Patent number
US06794517B2

Linked notes

Loading…