Lithium Hydroxide → HCID 118061706, compound

HRID 920799Notes

Reaction equation

HRID 920799 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2([C:15]([O:17]C)=[O:16])[CH2:12][C:11]([F:14])([F:13])[CH2:10]2)=[CH:5][CH:4]=1)#[N:2].[Li+].[OH-]>C1COCC1.O>[C:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2([C:15]([OH:17])=[O:16])[CH2:10][C:11]([F:14])([F:13])[CH2:12]2)=[CH:5][CH:4]=1)#[N:2]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 118061472HCID 118061472, compound

Product 1

HCID 118061706HCID 118061706, compoundYield 81.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of Intermediate 314E (300 mg, 1.194 mmol) in THF (2 mL) and water (2 mL) was added LiOH (57.2 mg, 2.388 mmol) and the reaction mixture was stirred at RT for 12 h. The reaction mixture was concentrated to remove THF and the aq. layer was acidified to a pH of 2 with a 1.5N aq. solution of HCl and extracted with EtOAc (3×15 mL) The combined organic layer was washed with brine, dried over Na2SO4, filtered and the filtrate concentrated to afford Intermediate 314F (230 mg, 81%) as a colorless semi-solid. 1H NMR (300 MHz, DMSO-d6) δ ppm 12.39 (br. s., 1H), 7.91-7.79 (m, 2H), 7.62-7.49 (m, 2H), 3.50-3.25 (m, 2H), 3.11 (d, J=14.0 Hz, 2H).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customto remove THF
  3. extractionextracted with EtOAc (3×15 mL) The combined organic layer
  4. washwas washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationthe filtrate concentrated

Sources & evidence

ORD record
ord-b5cf93a7785041268b1a49bf0076c93e
Source dataset
uspto-grants-2016_03
Patent number
US09273058B2

Reaction notes

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