Trifluoroacetic acid → HCID 11992569, compound

HRID 2241043Notes

Reaction equation

HRID 2241043 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[C:24]2[CH2:29][C:28]([CH3:31])([CH3:30])[CH2:27][C:26]([CH3:33])([CH3:32])[CH2:25]2)[C:9]2[CH:14]=[CH:13][C:12](/[CH:15]=[CH:16]/[C:17]([O:19]C(C)(C)C)=[O:18])=[CH:11][CH:10]=2)=[CH:4][CH:3]=1.C(C(O)=O)(F)(F)F>C(Cl)Cl>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[C:24]2[CH2:25][C:26]([CH3:33])([CH3:32])[CH2:27][C:28]([CH3:31])([CH3:30])[CH2:29]2)[C:9]2[CH:14]=[CH:13][C:12](/[CH:15]=[CH:16]/[C:17]([OH:19])=[O:18])=[CH:11][CH:10]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 131728144HCID 131728144, compound

Product 1

HCID 11992569HCID 11992569, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 26 (˜700 mg, a mixture obtained from the above) and CH2Cl2 (8 mL) was treated with CF3CO2H (2 mL) at RT. The reaction mixture stirred at RT under N2 for 1.5 h and then concentrated under reduced pressure to afford the crude product. The crude material was purified by column chromatography to afford 165 mg of the desired product 27 as a white solid. A portion (350 mg) of the starting triflate 25 was also recovered. Data for 27: 1H NMR (400 MHz, CD3OD): δ 7.64 (d, J=16.0 Hz, 1H), 7.52 (d, J=8.0 Hz, 2H), 7.21 (d, J=8.0 Hz, 2H), 7.18 (d, J=5.6 Hz, 1H), 7.16 (d, J=5.6 Hz, 1H), 7.00 (t, J=8.8 Hz, 2H), 6.44 (d, J=16.00 Hz, 1H), 1.99 (s, 2H), 1.97 (s, 2H), 1.31 (s, 2H), 0.93 (s, 12H). LCMS (APCI): m/z 391 (M−H)−.

Workup

  1. concentrationconcentrated under reduced pressure
  2. customto afford the crude product
  3. customThe crude material was purified by column chromatography

Sources & evidence

ORD record
ord-f8f9befdfdf9424fbd0b9841b1c1c8a5
Source dataset
uspto-grants-2010_05
Patent number
US07723393B2

Reaction notes

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