Trifluoroacetic acid → 3-(4-Carboxymethoxy-phenyl)-propionic acid benzyl ester

HRID 2170116Notes

Reaction equation

HRID 2170116 reaction equation
[CH2:1]([O:8][C:9](=[O:27])[CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][C:15]([O:18][CH2:19][C:20]([O:22]C(C)(C)C)=[O:21])=[CH:14][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH2:1]([O:8][C:9](=[O:27])[CH2:10][CH2:11][C:12]1[CH:13]=[CH:14][C:15]([O:18][CH2:19][C:20]([OH:22])=[O:21])=[CH:16][CH:17]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 667980173-(4-tert-Butoxycarbonylmethoxy-phenyl)-propionic acid benzyl ester

Product 1

HCID 667975903-(4-Carboxymethoxy-phenyl)-propionic acid benzyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-(4-tert-Butoxycarbonylmethoxy-phenyl)-propionic acid benzyl ester (step 1) (10 g, 27 mmol) in DCM (100 ml) was treated with TFA (20 ml) and heated at reflux for 4 h. The resulting mixture was concentrated in vacuo. The residue was dissolved in DCM and concentrated in vacuo a further four times until a viscous oil of the title compound was obtained.

Workup

  1. temperatureheated
  2. temperatureat reflux for 4 h
  3. concentrationThe resulting mixture was concentrated in vacuo
  4. dissolutionThe residue was dissolved in DCM
  5. concentrationconcentrated in vacuo a further four times until a viscous oil of the title compound
  6. customwas obtained

Sources & evidence

ORD record
ord-a97bcdf00205407082a1aa35e4d3ec30
Source dataset
uspto-grants-2015_06
Patent number
US09050339B2

Reaction notes

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