Lithium Hydroxide → HCID 68801865, compound

HRID 29016Notes

Reaction equation

HRID 29016 reaction equation
C([O:3][C:4](=[O:29])[CH2:5][CH2:6][CH2:7][O:8][C:9]1[CH:28]=[CH:27][C:12]2[NH:13][C:14](=[O:26])[O:15][C:16]([C:21]#[C:22][CH:23]3[CH2:25][CH2:24]3)([C:17]([F:20])([F:19])[F:18])[C:11]=2[CH:10]=1)C.[OH-].[Li+]>CO.O>[CH:23]1([C:22]#[C:21][C:16]2([C:17]([F:20])([F:19])[F:18])[O:15][C:14](=[O:26])[NH:13][C:12]3[CH:27]=[CH:28][C:9]([O:8][CH2:7][CH2:6][CH2:5][C:4]([OH:29])=[O:3])=[CH:10][C:11]2=3)[CH2:25][CH2:24]1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 688064764-(4-cyclopropylethynyl-2-oxo-4-trifluoromethyl-1,4-dihydro-2H-benzo[d][1,3]oxazin-6-yloxy)-butyric Acid Ethyl Ester

Product 1

HCID 68801865HCID 68801865, compoundYield 83%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a suspension of 45 mg (0.11 mmol) of 10 in 4 mL of 50% methanol in water was added 60 mg (2.5 mmol) of lithium hydroxide. The reaction mixture was allowed to stir at room temperature for 1 hour and concentrated under reduced pressure. To the residue 20 mL of water were added followed by 1 mL of 1N HCl. The reaction mixture was extracted with 4×30 mL of ethyl acetate. The organic layers were combined, dried (Na2SO4), and concentrated under reduced pressure. The residue was purified by preparative thin layer chromatography (silica gel, 2 mm thickness, E. Merck) using 5% methanol in dichloromethane to give 35 mg (0.091 mmol, 83%) of 11.

Workup

  1. concentrationconcentrated under reduced pressure
  2. additionTo the residue 20 mL of water were added
  3. extractionThe reaction mixture was extracted with 4×30 mL of ethyl acetate
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by preparative thin layer chromatography (silica gel, 2 mm thickness, E. Merck)

Sources & evidence

ORD record
ord-7420152c9db24ace8dcf6976799a9b2b
Source dataset
uspto-grants-2008_09
Patent number
US07420043B2

Reaction notes

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