Formamide → N-Formyl-L-phenylalanine

Reaction equation

[NH2:1][C@H:2]([C:10]([OH:12])=[O:11])[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[CH:13](N)=[O:14]>>[CH:13]([NH:1][C@H:2]([C:10]([OH:12])=[O:11])[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)=[O:14]

Participants

Reactant 2

HCID 713Formamide

HCID 6140L-Phenylalanine2×

Product 1

HCID 759256N-Formyl-L-phenylalanine

Procedure

Under a nitrogen atmosphere, a slurry of 1.65 gm (10 mmol) phenylalanine in 4.0 ml (100 mmol) formamide was heated at 90° C. for 45 minutes. Examination of the resulting homogeneous solution by proton NMR showed an 85% conversion of the phenylalanine to its N-formyl derivative.

Sources & evidence

ORD record: ord-698f8654597746aebff6e872ea39ebfe
Source dataset: uspto-grants-1988_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04789757

Reaction notes

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