Sodium Hydroxide → HCID 53475789, compound

HRID 1802544Notes

Reaction equation

HRID 1802544 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:10]=[C:11]([C:22]3([OH:32])[CH2:31][CH2:30][C:25]4(OCC[O:26]4)[CH2:24][CH2:23]3)[O:12][C:13]=2[C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)=[CH:5][CH:4]=1.[OH-].[Na+].C(=O)(O)[O-].[Na+]>O1CCCC1.Cl>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:10]=[C:11]([C:22]3([OH:32])[CH2:31][CH2:30][C:25](=[O:26])[CH2:24][CH2:23]3)[O:12][C:13]=2[C:14]2[CH:15]=[CH:16][C:17]([O:20][CH3:21])=[CH:18][CH:19]=2)=[CH:5][CH:4]=1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 516892Sodium BicarbonateHCID 67296295HCID 67296295, compound

Product 1

HCID 53475789HCID 53475789, compoundYield 63.5%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 8-(4,5-bis(4-methoxyphenyl)oxazol-2-yl)-1,4-dioxaspiro[4.5]decan-8-ol (Reference Example 92) (781 mg, 1.78 mmol) in tetrahydrofuran (4.5 mL), 6 M hydrochloric acid (9.0 mL) was added at 0° C., and the obtained solution was stirred at room temperature for 2 hours. The reaction solution was cooled to 0° C., and alkalified by addition of 10% aqueous sodium hydroxide solution and saturated sodium bicarbonate solution. The resulting solution was extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by recrystallization (ethyl acetate/n-hexane) to obtain the title compound (445 mg, 1.13 mmol, 63%) as a pale yellow solid.

Workup

  1. temperatureThe reaction solution was cooled to 0° C.
  2. extractionThe resulting solution was extracted with ethyl acetate
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by recrystallization (ethyl acetate/n-hexane)

Sources & evidence

ORD record
ord-e6c21eaa810c498c991f08f694f2c577
Source dataset
uspto-grants-2013_01
Patent number
US08349874B2

Reaction notes

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