Acetic Acid → N-Acetyl-L-valine

HRID 538953Notes

Reaction equation

HRID 538953 reaction equation
[NH2:1][C@H:2]([C:6]([OH:8])=[O:7])[CH:3]([CH3:5])[CH3:4].[C:9](O)(=[O:11])[CH3:10]>>[C:9]([NH:1][C@H:2]([C:6]([OH:8])=[O:7])[CH:3]([CH3:5])[CH3:4])(=[O:11])[CH3:10]

Participants

3

Reactant 2

HCID 176Acetic AcidHCID 6287L-Valine

Product 1

HCID 66789N-Acetyl-L-valineYield 83.5%

Conditions

Temperature
150 °C

Procedure

Valine (1 g, 8.53 mmol) and acetic acid (20 mL) were mixed together and heated at 150° C. in a microwave for one hour. The excess acetic acid was removed using a rotary evaporator. The residue was stirred in MTBE at ambient temperature for one hour. The mixture was filtered and the solid was washed with MTBE. The solid was dried in a vacuum oven at 60° C. The product was obtained as a white solid (1.13 grams, 83.5%). 1H NMR (500 MHz, DMSO-d6) δ ppm 0.74-0.98 (m, 6H), 1.81-1.96 (m, 3H), 1.97-2.18 (m, 1H), 4.13 (dd, 1H), 7.99 (d, 1H).

Workup

  1. customThe excess acetic acid was removed
  2. customa rotary evaporator
  3. filtrationThe mixture was filtered
  4. washthe solid was washed with MTBE
  5. customThe solid was dried in a vacuum oven at 60° C

Sources & evidence

ORD record
ord-b0bcc99e33484739b2db489eee4319df
Source dataset
uspto-grants-2014_10
Patent number
US08865920B2

Reaction notes

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