Diethyl Ether → 3-(Cyclopropylcarbamoyl)-isoxazole-4-carboxylic acid

HRID 467745

Reaction equation

HRID 467745 reaction equation
C([O:3][C:4]([C:6]1[C:7]([C:11](=[O:16])[NH:12][CH:13]2[CH2:15][CH2:14]2)=[N:8][O:9][CH:10]=1)=[O:5])C.[Li+].[OH-].C(OCC)C>C1COCC1.C(O)C>[CH:13]1([NH:12][C:11]([C:7]2[C:6]([C:4]([OH:5])=[O:3])=[CH:10][O:9][N:8]=2)=[O:16])[CH2:14][CH2:15]1

Participants

6

Reactant 3

HCID 3283Diethyl EtherHCID 3939Lithium HydroxideHCID 700979003-(Cyclopropylcarbamoyl)-isoxazole-4-carboxylic acid ethyl ester

Product 1

HCID 700967853-(Cyclopropylcarbamoyl)-isoxazole-4-carboxylic acidYield 88.3%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
20 °C

Procedure

To a solution of 3-(cyclopropylcarbamoyl)-isoxazole-4-carboxylic acid ethyl ester (600 mg, 2.68 mmol) in THF (7 ml) and ethanol (3 ml) was added LiOH (1M; 5.35 ml, 5.35 mmol) at 0-5° C. The mixture was stirred at 20° C. for 1 h, poured into 50 ml diethyl ether and extracted. The organic phase was washed with water. The combined aqueous phases were acidified with 1M HCl (6 ml) and extracted with dichloromethane. The organic layers were dried and evaporated to yield the product as yellow oil (464 mg, 80%).

Workup

  1. extractionextracted
  2. washThe organic phase was washed with water
  3. extractionextracted with dichloromethane
  4. customThe organic layers were dried
  5. customevaporated

Sources & evidence

ORD record
ord-cb1f1ea9fee24a9fab4b5e788f07155c
Source dataset
uspto-grants-2014_01
Patent number
US08623866B2

Linked notes

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