Lithium Hydroxide → HCID 86707793, compound

HRID 2174369Notes

Reaction equation

HRID 2174369 reaction equation
C([O:3][C:4]([CH:6]1[CH2:9][C:8]([F:34])([C:10]2[CH:15]=[CH:14][C:13]([C:16]3[CH2:20][C:19]([C:25]4[CH:30]=[C:29]([Cl:31])[C:28]([Cl:32])=[C:27]([Cl:33])[CH:26]=4)([C:21]([F:24])([F:23])[F:22])[O:18][N:17]=3)=[CH:12][CH:11]=2)[CH2:7]1)=[O:5])C.[OH-].[Li+]>CCO.O>[F:34][C:8]1([C:10]2[CH:15]=[CH:14][C:13]([C:16]3[CH2:20][C:19]([C:25]4[CH:26]=[C:27]([Cl:33])[C:28]([Cl:32])=[C:29]([Cl:31])[CH:30]=4)([C:21]([F:22])([F:23])[F:24])[O:18][N:17]=3)=[CH:12][CH:11]=2)[CH2:7][CH:6]([C:4]([OH:5])=[O:3])[CH2:9]1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 86707792HCID 86707792, compound

Product 1

HCID 86707793HCID 86707793, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 19096565Water ethanolSolvent

Procedure

To a stirred solution of 3-fluoro-3-{4-[5-(3,4,5-trichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-phenyl}-cyclobutanecarboxylic acid ethyl ester (non-polar compound from Preparation 5, 2 g, 3.72 mmol) in EtOH:H2O (1:1, 140 mL) was added lithium hydroxide (0.782 g, 18.62 mmol) at 0° C. Resulting reaction mixture was stirred at room temperature for 16 hours. After consumption of starting material, reaction mixture was concentrated in vacuo; suspension was diluted with water (100 mL) and Acidified with 1M HCl up to pH=2 at 0° C. Solid was precipitated out, which was filtered on Whatmann filter paper. Solid was dissolved in EtOAc (100 mL), dried over sodium sulphate, filtered and evaporated to afford solid. Solid was washed with n-pentane (3×5 mL), dried to afford white solid (1.6 g, 85%). 1H NMR (400 MHz, DMSO-d6) δ: 2.75 (d, J=8.72 Hz, 2H), 2.81 (d, J=8.68 Hz, 2H), 3.37-3.39 (m, 1H), 4.29-4.41 (m, 2H), 7.55 (d, J=8.12 Hz, 2H), 7.77 (d, J=8.12 Hz, 2H), 7.84 (s, 2H), 12.50 (bs, 1H); LC-MS (m/z): 507.80 (M−H).

Workup

  1. customResulting
  2. customreaction mixture
  3. customAfter consumption of starting material, reaction mixture
  4. concentrationwas concentrated in vacuo
  5. additionsuspension was diluted with water (100 mL)
  6. customAcidified with 1M HCl up to pH=2 at 0° C
  7. customSolid was precipitated out
  8. filtrationwhich was filtered on Whatmann
  9. filtrationfilter paper
  10. dissolutionSolid was dissolved in EtOAc (100 mL)
  11. dry with materialdried over sodium sulphate
  12. filtrationfiltered
  13. customevaporated
  14. customto afford solid
  15. washSolid was washed with n-pentane (3×5 mL)
  16. customdried

Sources & evidence

ORD record
ord-e75d62b6889240c4a9daecd39d355651
Source dataset
uspto-grants-2015_06
Patent number
US09061013B2

Reaction notes

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