Trifluoroacetic acid → HCID 18172399, compound

HRID 397101Notes

Reaction equation

HRID 397101 reaction equation
[CH2:1]([N:8]([CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([O:27][CH3:28])[CH:22]=1)[CH2:9][CH:10]([C:12]1[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=1)O)[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]([N:8]1[CH2:9][CH:10]([C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=2)[C:26]2[C:21](=[CH:22][C:23]([O:27][CH3:28])=[CH:24][CH:25]=2)[CH2:20]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 18172426HCID 18172426, compound

Product 1

HCID 18172399HCID 18172399, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-[benzyl-(3-methoxy-benzyl)-amino]-1-(4-methoxy-phenyl)-ethanol (16.23 g, 43.0 mmol, see Preparation 63) in CH2Cl2 (280 ml) was added TFA (40.0 g, 27.0 ml, 350 mmol). The mixture was refluxed overnight. The reaction mixture was allowed to cool to RT and poured onto ice-water containing sat. NaHCO3 (250 ml). The mixture was extracted with CH2Cl2 (3×150 ml) and the combined organics were dried over MgSO4, filtered, and concentrated in vacuo. Flash chromatography (SiO2, gradient elution 10-40% EtOAc/Hexanes) of the residue afforded the title product (7.67 g, 21.3 mmol, 50% yield).

Workup

  1. temperatureThe mixture was refluxed overnight
  2. additionpoured onto ice-water containing sat. NaHCO3 (250 ml)
  3. extractionThe mixture was extracted with CH2Cl2 (3×150 ml)
  4. dry with materialthe combined organics were dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. washFlash chromatography (SiO2, gradient elution 10-40% EtOAc/Hexanes) of the residue

Sources & evidence

ORD record
ord-89f72cd917bd470ca23220861ea4bf4c
Source dataset
uspto-grants-2003_08
Patent number
US06608203B2

Reaction notes

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