Lithium Hydroxide → HCID 86707793, compound

HRID 2174370Notes

Reaction equation

HRID 2174370 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 72%

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 (polar spot of Preparation 5, 1.2 g, 2.23 mmol) in EtOH:H2O (1:1, 80 mL) was added lithium hydroxide (0.469 g, 11.17 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, diluted with water (50 mL) and acidified using 1M HCl up to pH=2 at 0° C., solid was precipitated out. Resulting solid was filtered on Whatmann filter paper. Solid was dissolved in EtOAc (50 mL), dried over sodium sulphate, filtered and evaporated to afford solid, which was washed with n-pentane (3×3 mL) to afford white solid (0.820 g, 72%). 1H NMR (400 MHz, DMSO-d6) δ: 2.75-2.84 (m, 5H), 4.30-4.42 (m, 2H), 7.65 (d, J=8.20 Hz, 2H), 7.77 (d, J=8.16 Hz, 2H), 7.85 (s, 2H), 12.52 (bs, 1H); LC-MS (m/z): 507.90 (M−H).

Workup

  1. customResulting
  2. customreaction mixture
  3. customAfter consumption of starting material, reaction mixture
  4. concentrationwas concentrated in vacuo
  5. additiondiluted with water (50 mL)
  6. customat 0° C.
  7. customsolid was precipitated out
  8. customResulting solid
  9. filtrationwas filtered on Whatmann
  10. filtrationfilter paper
  11. dissolutionSolid was dissolved in EtOAc (50 mL)
  12. dry with materialdried over sodium sulphate
  13. filtrationfiltered
  14. customevaporated
  15. customto afford solid, which
  16. washwas washed with n-pentane (3×3 mL)

Sources & evidence

ORD record
ord-b93eceb7f5da442f9a18b664f83f4060
Source dataset
uspto-grants-2015_06
Patent number
US09061013B2

Reaction notes

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