Lithium Hydroxide → HCID 21908378, compound

HRID 1374619Notes

Reaction equation

HRID 1374619 reaction equation
[OH-:1].[Li+].[C:3]([O:7][C:8]([N:10]1[C:19]2[C:14](=[CH:15][C:16]([F:20])=[CH:17][CH:18]=2)[C:13]([CH3:22])([CH3:21])[CH2:12][C:11]1=[O:23])=[O:9])([CH3:6])([CH3:5])[CH3:4]>C1COCC1>[C:3]([O:7][C:8]([NH:10][C:19]1[CH:18]=[CH:17][C:16]([F:20])=[CH:15][C:14]=1[C:13]([CH3:22])([CH3:21])[CH2:12][C:11]([OH:23])=[O:1])=[O:9])([CH3:6])([CH3:5])[CH3:4]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 21908387HCID 21908387, compound

Product 1

HCID 21908378HCID 21908378, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

375 ml (0.75 mol) of an aqueous 2 M lithium hydroxide solution is added to a solution of 44 g (0.15 mol) of 1-tert-butoxycarbonyl-3,4-dihydro-4,4-dimethyl-6-fluoro-2-quinolone in 1l of THF. After 24 hours at room temperature, the batch is concentrated by evaporation, brought to pH 4 with 10% citric acid and extracted with ether. The combined organic extracts are washed with saturated NaCl, dried (Na2SO4) and concentrated by evaporation in a vacuum. Column chromatography of the residue on silica gel with hexane-ethyl acetate yields 34.0 g of 3-(2-tert-butoxycarbonylamino-5-fluorophenyl)-3-methylbutyric acid [1H-NMR (CDCl3), δ (ppm)=1.62 (br.s, 15H), 2.77 (s, 2H), 6.41 (br, 1H), 6.93 (td, 1H), 7.07 (dd, 1H), 7.20 (br, 1H)], which dissolves in 1 l of THF and is mixed at 0° C. with 17 ml (121 mmol) of triethylamine and 11.5 ml (121 mmol) of ethyl chloroformate. After 10 minutes at 0° C., 20.7 g (546 mmol) of sodium borohydride is added to it, and 1 l of MeOH is slowly added in drops to it. The batch is stirred for another 30 minutes at 0° C., concentrated by evaporation and diluted with ethyl acetate. It is washed with saturated NaCl, dried on Na2SO4 and purified by column chromatography on silica gel with hexane-ethyl acetate. Yield: 6.7 g.

Workup

  1. concentrationthe batch is concentrated by evaporation
  2. extractionextracted with ether
  3. washThe combined organic extracts are washed with saturated NaCl
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated by evaporation in a vacuum

Sources & evidence

ORD record
ord-3e75778b1b9a4d82a296e756094bc4b6
Source dataset
uspto-grants-2007_01
Patent number
US07166592B2

Reaction notes

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