Hydrochloric Acid → HCID 67312850, compound

HRID 2190486Notes

Reaction equation

HRID 2190486 reaction equation
[CH:1]1([C:4]([NH:6][C:7]2[O:8][C:9]3[CH:15]=[C:14]([O:16][C:17]4[CH:18]=[C:19]([CH:24]=[CH:25][CH:26]=4)[C:20]([O:22]C)=[O:21])[CH:13]=[CH:12][C:10]=3[N:11]=2)=[O:5])[CH2:3][CH2:2]1.[OH-].[Na+].Cl>CO.C1(C)C=CC=CC=1>[CH:1]1([C:4]([NH:6][C:7]2[O:8][C:9]3[CH:15]=[C:14]([O:16][C:17]4[CH:18]=[C:19]([CH:24]=[CH:25][CH:26]=4)[C:20]([OH:22])=[O:21])[CH:13]=[CH:12][C:10]=3[N:11]=2)=[O:5])[CH2:3][CH2:2]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 67311146HCID 67311146, compound

Product 1

HCID 67312850HCID 67312850, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 1140TolueneSolvent

Procedure

To a solution of methyl 3-({2-[(cyclopropylcarbonyl)amino]-1,3-benzooxazol-6-yl}oxy)benzoate (8.2 g) in methanol (300 mL) was added 8N aqueous sodium hydroxide solution (50 ml), and the mixture was stirred at room temperature for 2 days. To the reaction mixture was added 6N hydrochloric acid to adjust the pH to about 6.0, and the reaction mixture was concentrated under reduced pressure to about 100 mL. Ethyl acetate (200 mL) was added to the residue, and the mixture was washed with water (150 mL×2). The collected aqueous layer was extracted with ethyl acetate (100 mL×2), and the combined organic layers were dried over anhydrous magnesium sulfate. The insoluble material was filtered off, and the filtrate was concentrated under reduced pressure to give a brown amorphous substance. The obtained crude product was dissolved in toluene (150 mL) and 2-methylpropan-2-ol (100 mL), and the solvent was evaporated under reduced pressure. An azeotropic operation with toluene and 2-methylpropan-2-ol was further repeated twice to remove water from the crude product. The obtained brown amorphous substance (8.6 g) was used as the title compound in the next operation without a further purification.

Workup

  1. concentrationthe reaction mixture was concentrated under reduced pressure to about 100 mL
  2. additionEthyl acetate (200 mL) was added to the residue
  3. washthe mixture was washed with water (150 mL×2)
  4. extractionThe collected aqueous layer was extracted with ethyl acetate (100 mL×2)
  5. dry with materialthe combined organic layers were dried over anhydrous magnesium sulfate
  6. filtrationThe insoluble material was filtered off
  7. concentrationthe filtrate was concentrated under reduced pressure
  8. customto give a brown amorphous substance
  9. customThe obtained crude product
  10. custom2-methylpropan-2-ol (100 mL), and the solvent was evaporated under reduced pressure
  11. customto remove water from the crude product
  12. customThe obtained brown amorphous substance (8.6 g) was used as the title compound in the next operation without a further purification

Sources & evidence

ORD record
ord-51364feac1eb49be84ed8a16c98b21f7
Source dataset
uspto-grants-2012_12
Patent number
US08324395B2

Reaction notes

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