Piperidine → L-Phenylalanine

HRID 1976814Notes

Reaction equation

HRID 1976814 reaction equation
C([NH:18][C@H:19]([C:27]([OH:29])=[O:28])[CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)(OCC1C2C(=CC=CC=2)C2C1=CC=CC=2)=O.N1CCCCC1>CN(C=O)C>[NH2:18][C@H:19]([C:27]([OH:29])=[O:28])[CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

4

Reactant 2

HCID 8082PiperidineHCID 978331Fmoc-phenylalanine

Product 1

HCID 6140L-Phenylalanine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Wash Fmoc-phenylalanine on Sasrin resin (1.00 g, 0.69 mmol) with DMF (20 mL×2). Add 20% piperidine in DMF (20 mL), agitate for 5 minutes, and drain the solvent. Repeat two times for 15 minutes. Wash the residue with DMF (20 mL×5) and then CH2Cl2 (20 mL×5). Dry the resin in a vacuum oven at 40° C. for 20 hours to give title resin.

Workup

  1. waitRepeat two times for 15 minutes
  2. washWash the residue with DMF (20 mL×5)
  3. customDry the resin in a vacuum oven at 40° C. for 20 hours
  4. customto give title resin

Sources & evidence

ORD record
ord-1767389372f14f198f7fedf045473930
Source dataset
uspto-grants-2001_05
Patent number
US06228985B1

Reaction notes

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