Trifluoroacetic acid → 2-Methyl-2-(4-methylaminomethyl-phenoxy)-propionic acid ethyl ester

HRID 852398Notes

Reaction equation

HRID 852398 reaction equation
[CH2:1]([O:3][C:4](=[O:25])[C:5]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][N:16](C(OC(C)(C)C)=O)[CH3:17])=[CH:11][CH:10]=1)([CH3:7])[CH3:6])[CH3:2].C(O)(C(F)(F)F)=O>ClCCl>[CH2:1]([O:3][C:4](=[O:25])[C:5]([CH3:7])([O:8][C:9]1[CH:10]=[CH:11][C:12]([CH2:15][NH:16][CH3:17])=[CH:13][CH:14]=1)[CH3:6])[CH3:2]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 670722882-{4-[(tert-Butoxycarbonyl-methyl-amino)-methyl]-phenoxy}-2-methyl-propionic acid ethyl ester

Product 1

HCID 589070282-Methyl-2-(4-methylaminomethyl-phenoxy)-propionic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 3.66 g (10 mmol) of the above prepared 2-{4-[(tert-butoxycarbonyl-methyl-amino)-methyl]-phenoxy}-2-methyl-propionic acid ethyl ester in 50 ml dichloromethane was treated at 0° C. with 3.98 ml TFA and stirred at room temperature for 16 h. The reaction was evaporated and treated with ice water, neutralized with NaHCO3 (pH=8) and extracted dichloromethane (two times). The organic phases were washed with water, dried (MgSO4), and evaporated to give 2.77 g of crude product. Purification by flash chromatography on SiO2 with CH2Cl2/MeOH (95:5) yielded 1.95 g of the title compound as brown-yellow oil.

Workup

  1. customThe reaction was evaporated
  2. additiontreated with ice water
  3. extractionextracted dichloromethane (two times)
  4. washThe organic phases were washed with water
  5. dry with materialdried (MgSO4)
  6. customevaporated
  7. customto give 2.77 g of crude product
  8. customPurification by flash chromatography on SiO2 with CH2Cl2/MeOH (95:5)

Sources & evidence

ORD record
ord-148542d5ab1546c5b747522040c4df7b
Source dataset
uspto-grants-2007_08
Patent number
US07253192B2

Reaction notes

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