Cinchonidine → HCID 24959563, compound

HRID 2092500Notes

Reaction equation

HRID 2092500 reaction equation
[F:1][C:2]([C:7]1[CH:12]=[CH:11][C:10]([O:13][S:14]([C:17]([F:20])([F:19])[F:18])(=[O:16])=[O:15])=[CH:9][CH:8]=1)([CH3:6])[C:3]([OH:5])=[O:4].C=C[C@@H]1[C@@H]2C[C@@H]([C@H](O)C3C=CN=C4C=CC=CC=34)N(CC2)C1>CC(O)C>[F:1][C@:2]([C:7]1[CH:8]=[CH:9][C:10]([O:13][S:14]([C:17]([F:18])([F:20])[F:19])(=[O:16])=[O:15])=[CH:11][CH:12]=1)([CH3:6])[C:3]([OH:5])=[O:4]

Participants

4

Reactant 2

HCID 101744CinchonidineHCID 24959562HCID 24959562, compound

Product 1

HCID 24959563HCID 24959563, compoundYield 39,393.898%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To a solution of 1 (9.38 g, 29.7 mmol) in 2-propanol (150 ml), cinchonidine (8.73 g, 29.7 mmol) was added under vigorous stirring and the resulting mixture was left under reflux until to complete dissolution. After cooling at room temperature the formed precipitate was filtered off and the mother liquors were crystallized again from 2-propanol (50 mL). The collected precipitated salts (8.72 g) were dissolved in water (70 mL) and 37% HCl (2 mL) was added; the aqueous layer was extracted with CH2Cl2 (2×70 mL), dried over Na2SO4 and evaporated under vacuum to give the pure (2S)-2-fluoro-2-(4-{[(trifluoromethyl)sulfonyl]oxy}phenyl)propanoic acid (3.7 g, 11.7 mol) as pale brown solid. Yield 79%. mp 91-94° C. e.e. 96% (HPLC). [α]D=+19.8 (c=0.6; CH3OH). 1H-NMR (CDCl3) δ 7.70 (d, 2H, J=7 Hz), 7.40 (d, 2H, J=7 Hz), 2.00 (d, 3H, J=23 Hz).

Workup

  1. waitthe resulting mixture was left
  2. temperatureunder reflux until to complete dissolution
  3. filtrationwas filtered off
  4. customthe mother liquors were crystallized again from 2-propanol (50 mL)
  5. customThe collected precipitated salts (8.72 g)
  6. dissolutionwere dissolved in water (70 mL)
  7. addition37% HCl (2 mL) was added
  8. extractionthe aqueous layer was extracted with CH2Cl2 (2×70 mL)
  9. dry with materialdried over Na2SO4
  10. customevaporated under vacuum

Sources & evidence

ORD record
ord-48b2d69cfb9d4fe48ea8403d6e03f081
Source dataset
uspto-grants-2013_05
Patent number
US08440711B2

Reaction notes

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