2-Methyltetrahydrofuran → N-(2-(tert-Butyl)-5-hydroxy-4-(1-hydroxy-2-methylpropan-2-yl)phenyl)-4-oxo-1,4-dihydroquinoline-3-carboxamide

HRID 446144

Reaction equation

HRID 446144 reaction equation
[C:1]([C:5]1[C:6]([NH:17][C:18]([C:20]2[C:29](=[O:30])[C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[NH:22][CH:21]=2)=[O:19])=[CH:7][C:8]2[O:12][C:11](=[O:13])[C:10]([CH3:15])([CH3:14])[C:9]=2[CH:16]=1)([CH3:4])([CH3:3])[CH3:2].CC1OCCC1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.O.O.O.OC(C(O)C([O-])=O)C([O-])=O.[Na+].[K+]>CC(OC)(C)C>[C:1]([C:5]1[CH:16]=[C:9]([C:10]([CH3:15])([CH3:14])[CH2:11][OH:13])[C:8]([OH:12])=[CH:7][C:6]=1[NH:17][C:18]([C:20]1[C:29](=[O:30])[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[NH:22][CH:21]=1)=[O:19])([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 4

HCID 73012-MethyltetrahydrofuranHCID 2724148Sodium potassium tartrate tetrahydrateHCID 21226445Aluminium lithium hydrideHCID 59544159N-(5-(tert-Butyl)-3,3-dimethyl-2-oxo-2,3-dihydrobenzofuran-6-yl)-4-oxo-1,4-dihydroquinoline-3-carboxamide

Product 1

HCID 46897962N-(2-(tert-Butyl)-5-hydroxy-4-(1-hydroxy-2-methylpropan-2-yl)phenyl)-4-oxo-1,4-dihydroquinoline-3-carboxamide

Reagents, catalysts & solvents 1

HCID 15413tert-Butyl methyl etherSolvent

Procedure

A 3-neck 50 mL round bottom flask was equipped with magnetic stirrer, nitrogen bubbler and thermocouple. Compound 21 (514 mg, 1.27 mmol) and 2-MeTHF (4 mL) are charged to the flask. The reaction mixture was stirred at room temperature. Lithium aluminum hydride (204 mg, 6.6 mmol) was added as solid until 100% conversion is achieved, which was monitored using HPLC. Potassium sodium 2,3-dihydroxybutanedioate tetrahydrate salt (50 mL of a 400 g/L solution) and MTBE (50 mL) were added to the reaction mixture. The resulting solution was stirred for 15 minutes and then let sit for 15 min. The organic layer was separated and the pH of the aqueous layer was adjusted to a pH of about 6-7 by adding Tartaric acid. The aqueous layer was extracted with MTBE. The organic layer was concentrated and dried under high vacuum to provide the title compound as an off-white powder. The 1H-NMR spectrum was consistent with that reported above.

Workup

  1. customA 3-neck 50 mL round bottom flask was equipped with magnetic stirrer
  2. stirringThe resulting solution was stirred for 15 minutes
  3. customThe organic layer was separated
  4. additionby adding Tartaric acid
  5. extractionThe aqueous layer was extracted with MTBE
  6. concentrationThe organic layer was concentrated
  7. customdried under high vacuum

Sources & evidence

ORD record
ord-ca7e4a59bb0f46be8892546fbd47aa27
Source dataset
uspto-grants-2013_07
Patent number
US08476442B2

Linked notes

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