Formamide → N-Formyl-L-tyrosine

HRID 414134Notes

Reaction equation

[NH2:1][C@H:2]([C:11]([OH:13])=[O:12])[CH2:3][C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1.[CH:14](N)=[O:15]>>[CH:14]([NH:1][C@H:2]([C:11]([OH:13])=[O:12])[CH2:3][C:4]1[CH:5]=[CH:6][C:7]([OH:10])=[CH:8][CH:9]=1)=[O:15]

Participants

Reactant 2

HCID 713Formamide

HCID 6057L-Tyrosine2×

Product 1

HCID 13025455N-Formyl-L-tyrosine

Procedure

Under a nitrogen atmosphere, a slurry of 1.81 gm (10 mmol) tyrosine in 4.0 ml (100 mmol) formamide was heated at 90° C. for 19 hours and 10 minutes. Examination of the resulting homogeneous solution by proton NMR showed an 84% conversion of the tyrosine to its N-formyl derivative.

Sources & evidence

ORD record: ord-4842c3cd3bd64d55beae526ac76570de
Source dataset: uspto-grants-1988_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04789757

Reaction notes

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