Trifluoroacetic acid water → 3-[4-Hydroxy-2-(isopropoxycarbonylamino-methyl)-phenyl]-propionic acid methyl ester

HRID 1181042Notes

Reaction equation

HRID 1181042 reaction equation
[C:1]([O:5][C:6](=[O:24])[CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][C:10]=1[CH2:16][NH:17][C:18]([O:20][CH:21]([CH3:23])[CH3:22])=[O:19])(C)(C)C.C(C(O)=O)(F)(F)F.O>C(Cl)Cl>[CH3:1][O:5][C:6](=[O:24])[CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][C:10]=1[CH2:16][NH:17][C:18]([O:20][CH:21]([CH3:22])[CH3:23])=[O:19]

Participants

4

Reactant 2

HCID 22392675Trifluoroacetic acid waterHCID 589794703-[4-Hydroxy-2-(isopropoxycarbonylamino-methyl)-phenyl]-propionic acid tert-butyl ester

Product 1

HCID 589789623-[4-Hydroxy-2-(isopropoxycarbonylamino-methyl)-phenyl]-propionic acid methyl esterYield 86%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 3-[4-hydroxy-2-(isopropoxycarbonylamino-methyl)-phenyl]-propionic acid tert-butyl ester (3.0 mmol, 1.0 g) in CH2Cl2 (10 mL) was treated with 90% CF3CO2H/H2O (20 mL) at ambient temperature. The mixture was stirred for 3 h and concentrated. The residue was dissolved in MeOH (20 mL), treated with conc. H2SO4 (1 mL), and heated at reflux for 14 h. The mixture was cooled and concentrated. The residue was dissolved in water/ethyl acetate and neutralized with K2CO3. The organic layer was dried (Na2SO4), and concentrated to give the title compound (0.76 g, 86%). HRMS Calculated for C15H22NO5: m/z 296.1498. Found: 296.1504.

Workup

  1. concentrationconcentrated
  2. dissolutionThe residue was dissolved in MeOH (20 mL)
  3. additiontreated with conc. H2SO4 (1 mL)
  4. temperatureheated
  5. temperatureat reflux for 14 h
  6. temperatureThe mixture was cooled
  7. concentrationconcentrated
  8. dissolutionThe residue was dissolved in water/ethyl acetate and neutralized with K2CO3
  9. dry with materialThe organic layer was dried (Na2SO4)
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-8386ebfd23a44964a787484a7afc6a20
Source dataset
uspto-grants-2007_10
Patent number
US07282501B2

Reaction notes

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