Trifluoroacetic acid → HCID 11465090, compound

HRID 2118220Notes

Reaction equation

HRID 2118220 reaction equation
[C:1]1(/[C:7](/[CH2:35][CH3:36])=[C:8](/[C:20]2[CH:25]=[CH:24][C:23](/[CH:26]=[CH:27]/[C:28]([O:30]C(C)(C)C)=[O:29])=[CH:22][CH:21]=2)\[C:9]2[CH:14]=[CH:13][C:12]([O:15][P:16]([OH:19])([OH:18])=[O:17])=[CH:11][CH:10]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[C:1]1(/[C:7](/[CH2:35][CH3:36])=[C:8](/[C:20]2[CH:21]=[CH:22][C:23](/[CH:26]=[CH:27]/[C:28]([OH:30])=[O:29])=[CH:24][CH:25]=2)\[C:9]2[CH:10]=[CH:11][C:12]([O:15][P:16]([OH:19])([OH:18])=[O:17])=[CH:13][CH:14]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 58877663HCID 58877663, compound

Product 1

HCID 11465090HCID 11465090, compoundYield 87.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 36 (0.40 g) in CH2Cl2 (5 mL) at 0° C. was added dropwise TFA (5 mL) and the mixture was stirred at 0° C. for 2 h. Solvent was evaporated and coevaporated with CH2Cl2 (2×5 mL). The residue was suspended in Et2O/EtOAc (1:4 v/v, 10 mL) and treated with 1 M aqueous NaOH (10 mL). The aqueous phase was separated and acidified (pH ˜2-3) with aqueous HCl. The mixture was extracted with EtOAc and the organic layer was dried (Na2SO4) and concentrated. The resulting solid foam was dissolved in a small amount EtOAc and then excess hexanes added. After stirring for 20 min, the precipitate was filtered and washed with hexanes to provide 35 (0.31 g, 86%) as a pale yellow solid, mp 181-183° C. 1HNMR (CD3OD): δ 0.92 (t, J=7.1 Hz, 3H), 2.47 (q, J=7.1 Hz, 2H), 6.49 (d, J=16 Hz, 1H), 6.82-6.87 (m, 4H), 7.03-7.21 (m, 5H), 7.27 (d, J=7.8 Hz, 2H), 7.6 (d, J=7.8 Hz, 2H), 7.69 (d, J=16 Hz, 1H); 31PNMR (CD3OD): δ−4.06 (s); MS, m/z 473 (M+Na)+; Anal. calculated for C25H23O6P.0.36H2O: C, 65.72; H, 5.23; Found: C, 65.71; H, 5.33.

Workup

  1. customSolvent was evaporated
  2. additiontreated with 1 M aqueous NaOH (10 mL)
  3. customThe aqueous phase was separated
  4. extractionThe mixture was extracted with EtOAc
  5. dry with materialthe organic layer was dried (Na2SO4)
  6. concentrationconcentrated
  7. dissolutionThe resulting solid foam was dissolved in a small amount EtOAc
  8. additionexcess hexanes added
  9. stirringAfter stirring for 20 min
  10. filtrationthe precipitate was filtered
  11. washwashed with hexanes

Sources & evidence

ORD record
ord-dc10c640a5714b6db65483b4ebdf6af1
Source dataset
uspto-grants-2008_10
Patent number
US07442833B2

Reaction notes

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