Acetic Acid → N-Acetyl-L-phenylalanine

HRID 538951Notes

Reaction equation

HRID 538951 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.[C:13](O)(=[O:15])[CH3:14]>>[C: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:15])[CH3:14]

Participants

3

Reactant 2

HCID 176Acetic AcidHCID 6140L-Phenylalanine

Product 1

HCID 74839N-Acetyl-L-phenylalanineYield 78.4%

Conditions

Temperature
150 °C

Procedure

Phenylalanine (1 g, 6.05 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 taken up in toluene and the solvent was removed using a rotary evaporator. The residue was stirred in methyl t-butyl ether (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 (983 mg, 78.4%). 1H NMR (500 MHz, DMSO-d6) δ ppm 1.79 (s, 3H), 2.84 (dd, 1H), 3.05 (dd, 1H), 4.41 (td, 1H), 7.09-7.33 (m, 6H), 8.20 (d, 1H).

Workup

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

Sources & evidence

ORD record
ord-d2dc328dd5b6424eb9c4649e71f7b6b0
Source dataset
uspto-grants-2014_10
Patent number
US08865920B2

Reaction notes

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