Piperidine → 4-Acetyl-L-phenylalanine

HRID 2113407Notes

Reaction equation

HRID 2113407 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-phenylalanine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

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% TPA), 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 a obtain white solid (0.45 g, 88%). 1HNMR (D2O): δ 7.85-7.28 (m, 4H), 4.23 (dd, 1H, 5.4 Hz), 3.2 (m, 2H), 2.7 (s, 3H). LRMS, calcd for C11H13NO3 (M++1): 208.09. Found (ESI): 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-69630d1e99ca4412bfb99bb7c7ce1b4a
Source dataset
uspto-grants-2008_10
Patent number
US07432092B2

Reaction notes

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