Formic Acid → N-Formyl-L-valine

HRID 595530Notes

Reaction equation

HRID 595530 reaction equation
[C:1](OC(=O)C)(=[O:3])C.[NH2:8][C@H:9]([C:13]([OH:15])=[O:14])[CH:10]([CH3:12])[CH3:11].C(O)=O>>[CH:1]([NH:8][C@H:9]([C:13]([OH:15])=[O:14])[CH:10]([CH3:12])[CH3:11])=[O:3]

Participants

4

Reactant 3

HCID 284Formic AcidHCID 6287L-ValineHCID 7918Acetic Anhydride

Product 1

HCID 6950945N-Formyl-L-valine

Procedure

Acetic anhydride (4 mL, 0.04 mol) was added dropwise to a solution of L-Valine (1 g, 8.35 mmol) in formic acid (12 mL, 0.32 mol) while stirring on ice. The mixture was then warmed up to RT and kept stirring for 24 hours before the solvent was removed by rotary evaporation under high vacuum. The formyl-valine was recrystallized from ethyl acetate and the desired product was obtained as a white solid. Yield: 0.78 g (64%) 1HNMR (500 MHz, [D6]Acetone, 25° C., TMS): δ=8.22 (s, 1H), 7.41 (b, 1H), 4.50 (m, 1H), 2.22 (m, 1H), 0.98 (m, 6H).

Workup

  1. stirringkept stirring for 24 hours before the solvent
  2. customwas removed by rotary evaporation under high vacuum
  3. customThe formyl-valine was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-cdbce83ac5c0480294fc2152e54b4207
Source dataset
uspto-grants-2016_01
Patent number
US09243037B2

Reaction notes

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