Trifluoroacetic acid → HCID 66846592, compound

HRID 747918Notes

Reaction equation

HRID 747918 reaction equation
C(OC([N:8]1[CH2:15][CH:14]2[C:10]([CH3:26])([N:11]([C:16]([O:18][CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[O:17])[CH2:12][CH2:13]2)[CH2:9]1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH2:19]([O:18][C:16]([N:11]1[CH2:12][CH2:13][CH:14]2[CH2:15][NH:8][CH2:9][C:10]12[CH3:26])=[O:17])[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 66846317HCID 66846317, compound

Product 1

HCID 66846592HCID 66846592, compoundYield 55.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The product of Example 20F (0.8 g, 2.22 mmol) was treated with TFA (5 mL) in CH2Cl2 (10 mL) at ambient temperature for 1 h. The mixture was then concentrated under reduced pressure and the residue was purified by column chromatography (SiO2, 90: 9: 1 CH2Cl2: MeOH: NH4OH) to give the title compound (0.32 g, 1.23 mmol, 55% yield). 1H NMR (MeOH-d4, 300 MHz) δ 1.42, 1.47 (s, 3H, rotamers), 1.63-1.75 (m, 1H), 1.98-2.13 (m, 1H), 2.37-2.52 (m, 1H), 2.62-2.76 (m, 2H), 3.00-3.12 (m, 1H), 3.26, 3.47 (d, J=12.6 Hz, 1H, rotamers), 3.53-3.62 (m, 2H), 5.08, 5.13 (s, 2H, rotamers), 7.25-7.42 (m, 5H); MS (DCl/NH3) m/z 261 (M+H)+.

Workup

  1. concentrationThe mixture was then concentrated under reduced pressure
  2. customthe residue was purified by column chromatography (SiO2, 90: 9: 1 CH2Cl2: MeOH: NH4OH)

Sources & evidence

ORD record
ord-042f331100fe4af6918bab9c8a904ec4
Source dataset
uspto-grants-2008_07
Patent number
US07399765B2

Reaction notes

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