Trifluoroacetic acid → HCID 59855128, compound

HRID 2375736Notes

Reaction equation

HRID 2375736 reaction equation
FC(F)(F)C(O)=O.[CH3:8][N:9]1[CH:13]=[CH:12][N:11]=[C:10]1[CH:14]([C:21]1[CH:26]=[CH:25][C:24]([O:27]C2CCCCO2)=[CH:23][CH:22]=1)[CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17]>C(Cl)Cl>[OH:27][C:24]1[CH:25]=[CH:26][C:21]([CH:14]([C:10]2[N:9]([CH3:8])[CH:13]=[CH:12][N:11]=2)[CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:22][CH:23]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59855135HCID 59855135, compound

Product 1

HCID 59855128HCID 59855128, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Trifluoroacetic acid (21 mL) was added to a solution of protected ester 9.4 (21 g) in dry DCM (210 mL) with caution at 0° C. The mixture was brought to room temperature over 4 hours. The reaction mixture was concentrated under reduced pressure to provide a yellow oily residue, which was re-dissolved in DCM (200 mL) and washed with water, saturated NaHCO3, water and brine, and dried over Na2SO4. After filtration, the solvent was removed under reduced pressure, and the product was crystallized in EtOAc-hexane. The mother liquid was concentrated and flash chromatographed (silica gel, 50% EtOAc in hexane as eluant). The product, (±)-ethyl 3-(4-hydroxyphenyl)-3-(1-methyl-1H-imidazol-2-yl)propanoate (9.5) was obtained as a colorless crystal (combined yield 11 g). LC-MS ESI (pos.) m/e: 275 (M+H). 1H NMR (500 MHz) (CDCl3) δ 9.28 (s, 1H); 6.98-7.00 (m, 3H); 6.65-6.77(m, 3H); 4.41 (dd, J=9.0, 3.0 Hz, 1H); 3.96 (q, J=7.0, 2H); 3.39 (s, 3H); 3.19 (dd, J=16.0, 7.0 Hz, 1H); 2.78 (dd, J=16.0, 6.5 Hz, 1H); 1.80 (t, J=7.0 Hz, 3H).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customto provide a yellow oily residue, which
  3. washwashed with water, saturated NaHCO3, water and brine
  4. dry with materialdried over Na2SO4
  5. filtrationAfter filtration
  6. customthe solvent was removed under reduced pressure
  7. customthe product was crystallized in EtOAc-hexane
  8. concentrationThe mother liquid was concentrated
  9. customflash chromatographed (silica gel, 50% EtOAc in hexane as eluant)

Sources & evidence

ORD record
ord-767e89362cac4717af05fd66d8f914f3
Source dataset
uspto-grants-2008_12
Patent number
US07465804B2

Reaction notes

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