L-Valine → N-Formyl-DL-valine

HRID 543900Notes

Reaction equation

HRID 543900 reaction equation
[NH2:1][C@H:2]([C:6]([OH:8])=[O:7])[CH:3]([CH3:5])[CH3:4].[CH:9](OC(=O)C)=[O:10]>C(O)=O>[CH:9]([NH:1][CH:2]([CH:3]([CH3:5])[CH3:4])[C:6]([OH:8])=[O:7])=[O:10]

Participants

4

Reactant 2

HCID 6287L-ValineHCID 75269Acetic-formic anhydride

Product 1

HCID 100123N-Formyl-DL-valine

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

To valine (15 g, 0.129 mol) in 88% formic acid (52 ml) is added acetic formic anhydride (33 g, 0.386 mol) over 0.75 hr at 5°. The reaction mixture is warmed to RT and stirred overnight. The reaction is worked up by distilling off (bath temp. 45°-50°) the solvent, excess anhydride and acetic acid, to give, as a white solid, 2-(N-formylamino)-3-methylbutanoic acid, recrystallized from hot ethanol, m.p. 143°-145°.

Workup

  1. distillationby distilling off (bath temp. 45°-50°) the solvent, excess anhydride and acetic acid

Sources & evidence

ORD record
ord-ce1abaa5b24947e19a19a27b5a99ae14
Source dataset
uspto-grants-1984_05
Patent number
US04447613

Reaction notes

Loading…