Trifluoroacetic acid → 5-Cyclopropyl-2-fluoro-4-((4-fluorobicyclo[4.1.0]heptan-1-yl)methoxy)benzoic acid
Reaction equation
[CH:1]1([C:4]2[C:5]([O:18][CH2:19][C:20]34[CH2:26][CH:25]3[CH2:24][CH:23](O)[CH2:22][CH2:21]4)=[CH:6][C:7]([F:17])=[C:8]([CH:16]=2)[C:9]([O:11]C(C)(C)C)=[O:10])[CH2:3][CH2:2]1.C(N(S(F)(F)[F:34])CC)C.FC(F)(F)C(O)=O>C(Cl)(Cl)Cl>[CH:1]1([C:4]2[C:5]([O:18][CH2:19][C:20]34[CH2:26][CH:25]3[CH2:24][CH:23]([F:34])[CH2:22][CH2:21]4)=[CH:6][C:7]([F:17])=[C:8]([CH:16]=2)[C:9]([OH:11])=[O:10])[CH2:2][CH2:3]1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of tert-butyl 5-cyclopropyl-2-fluoro-4-((4-hydroxybicyclo-[4.1.0]heptan-1-yl)methoxy)benzoate (0.13 g, 0.41 mmol) in chloroform (2 mL) was added diethylaminosulfur trifluoride (0.11 mL, 0.89 mmol). The reaction solution was stirred at ambient temperature for 16 h and quenched with slow addition of aqueous saturated sodium hydrogencarbonate. The reaction mixture was extracted with dichloromethane. The solvent was concentrated in vacuo to dryness. The residue (0.10 g) was dissolved in dichloromethane (1 mL) and trifluoroacetic acid (0.15 g, 1.30 mmol) was added. The reaction mixture was stirred for 2 h and the solvent was concentrated in vacuo to obtain the title compound as a gum (0.080 g, 95%). The residue was carried forward without any further purification in next reaction: MS (ES−) m/z 321.1 (M−1).
Workup
- customquenched with slow addition of aqueous saturated sodium hydrogencarbonate
- extractionThe reaction mixture was extracted with dichloromethane
- concentrationThe solvent was concentrated in vacuo to dryness
- dissolutionThe residue (0.10 g) was dissolved in dichloromethane (1 mL)
- stirringThe reaction mixture was stirred for 2 h
- concentrationthe solvent was concentrated in vacuo
Sources & evidence
- ORD record
- ord-4e5dc768396a4f978736ecd92ccd431b
- Source dataset
- uspto-grants-2015_02
- Patent number
- US08952169B2
Reaction notes
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