Trifluoroacetic acid → 1-Cbz-Piperidin-4-ylidene-acetic acid

HRID 1584375Notes

Reaction equation

HRID 1584375 reaction equation
F[C:2](F)(F)[C:3]([OH:5])=[O:4].C(OC([CH:15]1[CH2:20][CH2:19][N:18]([C:21]([O:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[O:22])[C:17](=C)[CH2:16]1)=O)(C)(C)C>C(Cl)Cl>[C:3]([CH:2]=[C:15]1[CH2:20][CH2:19][N:18]([C:21]([O:23][CH2:24][C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)=[O:22])[CH2:17][CH2:16]1)([OH:5])=[O:4]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 700523534-tert-butoxycarbonyl-methylene-N-CBZ-piperidine

Product 1

HCID 212243161-Cbz-Piperidin-4-ylidene-acetic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (10 ml) was added to 4-tert-butoxycarbonyl-methylene-N-CBZ-piperidine (20 g, 60.3 mmol) in methylene chloride (30 ml) and the solution was stirred at room temperature for 1.5 hours. After evaporation of the solvent, the residue was triturated with diethyl ether to give 4-carboxymethylene-N-CBZ-piperidine as a crystalline white solid.

Workup

  1. customAfter evaporation of the solvent
  2. customthe residue was triturated with diethyl ether

Sources & evidence

ORD record
ord-c3f956a665ca46118e18c72907f9c2cc
Source dataset
uspto-grants-1999_08
Patent number
US05932595

Reaction notes

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