Hydrochloric Acid → HCID 90202440, compound

HRID 929758Notes

Reaction equation

HRID 929758 reaction equation
C([O:3][C:4]([C:6]1[O:10][N:9]=[C:8]([C:11]2[CH:16]=[CH:15][C:14]([O:17][CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[Cl:25])=[CH:13][N:12]=2)[CH:7]=1)=[O:5])C.Cl>[OH-].[K+].C1COCC1>[Cl:25][C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=1[CH2:18][O:17][C:14]1[CH:15]=[CH:16][C:11]([C:8]2[CH:7]=[C:6]([C:4]([OH:5])=[O:3])[O:10][N:9]=2)=[N:12][CH:13]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 90202331HCID 90202331, compound2×

Product 1

HCID 90202440HCID 90202440, compoundYield 100.8%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 14797Potassium HydroxideSolvent

Conditions

Temperature
55 °C

Procedure

Crude 3-[5-(2-Chloro-benzyloxy)-pyridin-2-yl]-isoxazole-5-carboxylic acid ethyl ester (which may be prepared as described in Preparation of Intermediate 9; 236 mg, 0.66 mmol assumed) was taken up in a mixture of 2 M KOH (12 mL) and THF (3 mL). The mixture was heated at 55° C. for 4 h and then stirred at room temperature overnight. The mixture was cooled to 0° C. and 4 M aqueous HCl (3 mL) was added. The mixture was extracted with EtOAc and the organic layer was dried (Na2SO4), filtered, and evaporated to give 3-[5-(2-chloro-benzyloxy)-pyridin-2-yl]-isoxazole-5-carboxylic acid (220 mg, 100%) as an off-white powder.

Workup

  1. temperatureThe mixture was cooled to 0° C.
  2. extractionThe mixture was extracted with EtOAc
  3. dry with materialthe organic layer was dried (Na2SO4)
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-eeb8ab78fd5f4f4aa836b7f3cb1e27ad
Source dataset
uspto-grants-2016_03
Patent number
US09296711B2

Reaction notes

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