Trifluoroacetic acid → HCID 86703558, compound

HRID 1849687Notes

Reaction equation

HRID 1849687 reaction equation
[CH:1]1([C:4]2[C:5]([O:18][CH2:19][C:20]3([CH3:30])[CH2:29][CH2:28][C:23]4(OCC[O:24]4)[CH2:22][CH2:21]3)=[CH:6][C:7]([F:17])=[C:8]([CH:16]=2)[C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:3][CH2:2]1.FC(F)(F)C(O)=O>O1CCCC1.O>[CH:1]1([C:4]2[C:5]([O:18][CH2:19][C:20]3([CH3:30])[CH2:29][CH2:28][C:23](=[O:24])[CH2:22][CH2:21]3)=[CH:6][C:7]([F:17])=[C:8]([CH:16]=2)[C:9]([O:11][C:12]([CH3:13])([CH3:14])[CH3:15])=[O:10])[CH2:2][CH2:3]1

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86703557HCID 86703557, compound

Product 1

HCID 86703558HCID 86703558, compoundYield 90.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of tert-butyl 5-cyclopropyl-2-fluoro-4-((8-methyl-1,4- dioxaspiro[4.5]decan-8-yl)methoxy)benzoate (2.59 g, 6.16 mmol) in tetrahydrofuran (6 mL) and water (4.3 mL) was added trifluoroacetic acid (2.2 mL, 27.72 mmol). The reaction mixture was stirred at ambient temperature for 18 hours. The reaction was quenched with 2 M aqueous sodium hydroxide solution (5 mL) before being diluted with saturated aqueous sodium bicarbonate (20 mL) and ethyl acetate (50 mL). The aqueous layer was separated and extracted with ethyl acetate (3×50 mL). The combined organics were dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. Purification of the residue by column chromatography (0% to 15% ethyl acetate in hexanes) afforded the title compound (2.09 g, 90%) as a colorless oil: MS (ES+) m/z 321.2 (M−55).

Workup

  1. customThe reaction was quenched with 2 M aqueous sodium hydroxide solution (5 mL)
  2. additionbefore being diluted with saturated aqueous sodium bicarbonate (20 mL) and ethyl acetate (50 mL)
  3. customThe aqueous layer was separated
  4. extractionextracted with ethyl acetate (3×50 mL)
  5. dry with materialThe combined organics were dried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customPurification of the residue by column chromatography (0% to 15% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-6413fcc0a8fe488580b2ce77485028de
Source dataset
uspto-grants-2015_02
Patent number
US08952169B2

Reaction notes

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