Triethylsilane → 3-[4-(2-Aminoethoxy)phenyl]-2-ethoxypropionic acid ethyl ester

HRID 1744456Notes

Reaction equation

HRID 1744456 reaction equation
[CH2:1]([O:3][C:4](=[O:28])[CH:5]([O:25][CH2:26][CH3:27])[CH:6]([C:8]1[CH:13]=[CH:12][C:11]([O:14][CH2:15][CH2:16][NH:17]C(OC(C)(C)C)=O)=[CH:10][CH:9]=1)O)[CH3:2].C([SiH](CC)CC)C>FC(F)(F)C(O)=O.C(OCC)(=O)C>[CH2:1]([O:3][C:4](=[O:28])[CH:5]([O:25][CH2:26][CH3:27])[CH2:6][C:8]1[CH:13]=[CH:12][C:11]([O:14][CH2:15][CH2:16][NH2:17])=[CH:10][CH:9]=1)[CH3:2]

Participants

5

Reactant 2

HCID 12052TriethylsilaneHCID 696255813-[4-(2-Tert-butoxycarbonylaminoethoxy)phenyl]-2-ethoxy-3-hydroxypropionic acid ethyl ester

Product 1

HCID 108589313-[4-(2-Aminoethoxy)phenyl]-2-ethoxypropionic acid ethyl esterYield 73.9%

Reagents, catalysts & solvents 2

HCID 6422Trifluoroacetic acidSolventHCID 8857Ethyl AcetateSolvent

Procedure

The compound obtained in Step b (53.7 mg) was dissolved in trifluoroacetic acid (2 ml), added with triethylsilane (0.4 ml, Aldrich) and stirred at room temperature for 2.5 days. The reaction mixture was diluted with ethyl acetate, washed successively with saturated aqueous sodium hydrogencarbonate and saturated brine, dried over magnesium sulfate and concentrated. The resulting residue was applied on a silica gel column and eluted with chloroform/methanol (10:1) to obtain the title compound (28.1 mg).

Workup

  1. washwashed successively with saturated aqueous sodium hydrogencarbonate and saturated brine
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated
  4. washeluted with chloroform/methanol (10:1)

Sources & evidence

ORD record
ord-9af7608ca2534abc877ee964af2b0668
Source dataset
uspto-grants-2006_03
Patent number
US07015345B2

Reaction notes

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