Lithium hydroxide, monohydrate → 4-[4-Methoxy-3-(3,3,6,6-tetramethyl-1,8-dioxo-2,3,4,5,6,7,8,9-octahydro-1H-xanthen-9-yl)phenyl]pyridine-2-carboxylic acid

HRID 873515Notes

Reaction equation

HRID 873515 reaction equation
O.[OH-].[Li+].[CH3:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH:17]=[CH:16][N:15]=[C:14]([C:18]([O:20]C)=[O:19])[CH:13]=2)=[CH:8][C:7]=1[CH:22]1[C:35]2[C:34](=[O:36])[CH2:33][C:32]([CH3:38])([CH3:37])[CH2:31][C:30]=2[O:29][C:28]2[CH2:27][C:26]([CH3:40])([CH3:39])[CH2:25][C:24](=[O:41])[C:23]1=2>O.C1COCC1>[CH3:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH:17]=[CH:16][N:15]=[C:14]([C:18]([OH:20])=[O:19])[CH:13]=2)=[CH:8][C:7]=1[CH:22]1[C:35]2[C:34](=[O:36])[CH2:33][C:32]([CH3:37])([CH3:38])[CH2:31][C:30]=2[O:29][C:28]2[CH2:27][C:26]([CH3:40])([CH3:39])[CH2:25][C:24](=[O:41])[C:23]1=2

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 117700520Methyl 4-[4-methoxy-3-(3,3,6,6-tetramethyl-1,8-dioxo-2,3,4,5,6,7,8,9-octahydro-1H-xanthen-9-yl)phenyl]pyridine-2-carboxylate

Product 1

HCID 1177006334-[4-Methoxy-3-(3,3,6,6-tetramethyl-1,8-dioxo-2,3,4,5,6,7,8,9-octahydro-1H-xanthen-9-yl)phenyl]pyridine-2-carboxylic acidYield 73.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

A solution of lithium hydroxide monohydrate (21.7 mg, 0.52 mmol) in water (2.4 ml) was added to a solution of the methyl 4-[4-methoxy-3-(3,3,6,6-tetramethyl-1,8-dioxo-2,3,4,5,6,7,8,9-octahydro-1H-xanthen-9-yl)phenyl]pyridine-2-carboxylate produced in Example 2-1 (121 mg, 0.23 mmol) in THF (4.8 ml) at room temperature, and the mixed solution was then stirred at the same temperature as above for 1 hour. Thereafter, water was added to the reaction solution, and the mixed solution was then washed with diethyl ether. A 1 N aqueous solution of hydrochloric acid (0.52 ml) was added to the water layer, and the mixed solution was then extracted with dichloromethane four times. The organic layer thus obtained was dried over anhydrous sodium sulfate. Thereafter, the solvent was distilled away under reduced pressure, and the residue thus obtained was then washed with a mixed solution of diethyl ether and hexane, followed by collection by filtration and drying, to obtain the title compound (84.5 mg, yield: 72%).

Workup

  1. washthe mixed solution was then washed with diethyl ether
  2. additionA 1 N aqueous solution of hydrochloric acid (0.52 ml) was added to the water layer
  3. extractionthe mixed solution was then extracted with dichloromethane four times
  4. customThe organic layer thus obtained
  5. dry with materialwas dried over anhydrous sodium sulfate
  6. distillationThereafter, the solvent was distilled away under reduced pressure
  7. customthe residue thus obtained
  8. washwas then washed with a mixed solution of diethyl ether and hexane
  9. filtrationfollowed by collection by filtration
  10. customdrying

Sources & evidence

ORD record
ord-bf1cc475514b4912a5653d0a5607651c
Source dataset
uspto-grants-2015_03
Patent number
US08975263B2

Reaction notes

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