Sodium Hydroxide → HCID 58476273, compound

HRID 1801398Notes

Reaction equation

HRID 1801398 reaction equation
C[O:2][C:3](=[O:30])[C:4]([CH3:29])([O:6][C:7]1[CH:8]=[C:9]([CH:13]2[C:22]([CH3:24])([CH3:23])[CH2:21][C:20]3[C:15](=[CH:16][CH:17]=[C:18]([C:25]([O:27]C)=[O:26])[CH:19]=3)[NH:14]2)[CH:10]=[CH:11][CH:12]=1)[CH3:5].[OH-].[Na+]>CO.O1CCCC1>[C:3]([C:4]([O:6][C:7]1[CH:8]=[C:9]([CH:13]2[C:22]([CH3:23])([CH3:24])[CH2:21][C:20]3[C:15](=[CH:16][CH:17]=[C:18]([C:25]([OH:27])=[O:26])[CH:19]=3)[NH:14]2)[CH:10]=[CH:11][CH:12]=1)([CH3:29])[CH3:5])([OH:30])=[O:2]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 67439980HCID 67439980, compound

Product 1

HCID 58476273HCID 58476273, compoundYield 30.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 2-(3-(1-methoxy-2-methyl-1-oxopropan-2-yloxy)phenyl)-3,3-dimethyl-1,2,3,4-tetrahydroquinoline-6-carboxylate (216 mg, 0.52 mmol) in methanol (8 mL) and tetrahydrofuran (8 mL) was added a 1 M solution of sodium hydroxide (7.87 mL). The mixture was stirred and heated to reflux for 1.5 h. The mixture was concentrated, dissolved in water and acidified to pH=4 with 1M hydrochloric acid. The precipitated solid was filtered and redissolved in tetrahydrofuran, and the organic layers were dried over anhydrous magnesium sulfate. After evaporation of the organic solvent, the residue was treated with dichloromethane to afford 60 mg of 2-(3-(2-carboxypropan-2-yloxy)phenyl)-3,3-dimethyl-1,2,3,4-tetrahydroquinoline-6-carboxylic acid as a white solid. Isolated yield: 30%; MS (ESI+APCI) M+1=384.

Workup

  1. temperatureheated
  2. temperatureto reflux for 1.5 h
  3. concentrationThe mixture was concentrated
  4. dissolutiondissolved in water
  5. filtrationThe precipitated solid was filtered
  6. dissolutionredissolved in tetrahydrofuran
  7. dry with materialthe organic layers were dried over anhydrous magnesium sulfate
  8. customAfter evaporation of the organic solvent
  9. additionthe residue was treated with dichloromethane

Sources & evidence

ORD record
ord-be5e64bf0fd9465a8cec47c7e034a256
Source dataset
uspto-grants-2013_01
Patent number
US08344137B2

Reaction notes

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