Trifluoroacetic acid → HCID 11442092, compound

HRID 2118224Notes

Reaction equation

HRID 2118224 reaction equation
[CH2:1]([O:3][C:4]([O:6][C:7]1[CH:12]=[CH:11][C:10](/[C:13](/[C:23]2[CH:28]=[CH:27][C:26](/[CH:29]=[CH:30]/[C:31]([O:33]C(C)(C)C)=[O:32])=[CH:25][CH:24]=2)=[C:14](\[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)/[CH2:15][CH3:16])=[CH:9][CH:8]=1)=[O:5])[CH3:2].C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH2:1]([O:3][C:4]([O:6][C:7]1[CH:8]=[CH:9][C:10](/[C:13](/[C:23]2[CH:28]=[CH:27][C:26](/[CH:29]=[CH:30]/[C:31]([OH:33])=[O:32])=[CH:25][CH:24]=2)=[C:14](\[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)/[CH2:15][CH3:16])=[CH:11][CH:12]=1)=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86612489HCID 86612489, compound

Product 1

HCID 11442092HCID 11442092, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 39 (0.51 g, 1.02 mmol) in CH2Cl2 (5 mL) at 0° C. was added TFA (5 mL) and the mixture was stirred for 1 h. Solvent was evaporated and coevaporated with CH2Cl2 (2×10 mL) and the residue dissolved in EtOAc and washed with water (2×10 mL). The organic layer was dried (Na2SO4) and evaporated. The residue was triturated with hexanes, filtered, and dried in vacuo to provide 37 (0.43 g, 96%) as an off-white solid. 1H NMR and MS as described in Example 23. Anal. calculated for C28H26O5: C, 76.00; H, 5.92; Found: C, 75.90; H, 6.12.

Workup

  1. customSolvent was evaporated
  2. dissolutionthe residue dissolved in EtOAc
  3. washwashed with water (2×10 mL)
  4. dry with materialThe organic layer was dried (Na2SO4)
  5. customevaporated
  6. customThe residue was triturated with hexanes
  7. filtrationfiltered
  8. customdried in vacuo

Sources & evidence

ORD record
ord-ba778425edd94287904cacb3c9da8e06
Source dataset
uspto-grants-2008_10
Patent number
US07442833B2

Reaction notes

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