Reaction #2075711

Reaction equation

Fmoc-4-acetyl-L-phenylalanine

piperidine

→

solid

Yield 88.0%

p-acetyl-L-phenylalanine

Yield 88.0%

Solvents

water

Conditions

Workup

1. 1
   OtherThe solvent was evaporated
2. 2
   Otherto obtain white powder
3. 3
   Filtrationthe supernatant was collected by filtration
4. 4
   Otherto separate the desired product from the reaction mixture (5-30% CH3CN in H2O with 0.1% TFA over 30 min)

Procedure

Fmoc-4-acetyl-L-phenylalanine was purchased from RSP Amino Acid Analogues, Inc. (Worcester, Mass.). This compound (1.0 g, 2.3 mmol) was stirred with 4 mL of piperidine (20% in DMF) for 2 hours at room temperature. The solvent was evaporated to obtain white powder. The solid was then resuspended in 10 mL of cold water (0.1% TFA), and the supernatant was collected by filtration. Preparative reverse-phase HPLC (Microsorb C18, Rainin Instrument Co., Inc., Woburn, Mass.) was used to separate the desired product from the reaction mixture (5-30% CH3CN in H2O with 0.1% TFA over 30 min). The eluant (tR=12 min) was lyophilized to obtain a white solid (0.45 g, 88%). 1H NMR (400 MHz D2O): δ 7.85-7.28 (m, 4H), 4.23 (dd, 1H, 5.4 Hz), 3.2 (m, 2H), 2.7 (s, 3H). MS (ESI): [M+1]+ calculated for C11H13NO3 208.09, found 208.47.

Source