Piperidine → 4-Acetyl-L-phenylalanine

HRID 855486Notes

Reaction equation

HRID 855486 reaction equation
C([NH:18][C@H:19]([C:30]([OH:32])=[O:31])[CH2:20][C:21]1[CH:26]=[CH:25][C:24]([C:27](=[O:29])[CH3:28])=[CH:23][CH:22]=1)(OCC1C2C(=CC=CC=2)C2C1=CC=CC=2)=O.N1CCCCC1>O>[C:27]([C:24]1[CH:25]=[CH:26][C:21]([CH2:20][C@@H:19]([C:30]([OH:32])=[O:31])[NH2:18])=[CH:22][CH:23]=1)(=[O:29])[CH3:28]

Participants

4

Reactant 2

HCID 8082PiperidineHCID 20821099HCID 20821099, compound

Product 1

HCID 64201234-Acetyl-L-phenylalanineYield 88%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Fmoc-p-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 dimethyl formamide (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% trifluoroacetic acid (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 electrospray ionization (ESI): [M+1]+ calcd for C11H13NO3 208.09, found 208.47.

Workup

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

Sources & evidence

ORD record
ord-5639c3e48acf47a89ed6c9d35625277c
Source dataset
uspto-grants-2007_08
Patent number
US07262040B2

Reaction notes

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