Sodium Hydroxide → 5-(Cyclopropylcarbamoyl)isoxazole-3-carboxylic acid

HRID 1409382Notes

Reaction equation

HRID 1409382 reaction equation
[CH:1]1([NH:4][C:5]([C:7]2[O:11][N:10]=[C:9]([C:12]([O:14]CC)=[O:13])[CH:8]=2)=[O:6])[CH2:3][CH2:2]1.[OH-].[Na+]>C(O)C>[CH:1]1([NH:4][C:5]([C:7]2[O:11][N:10]=[C:9]([C:12]([OH:14])=[O:13])[CH:8]=2)=[O:6])[CH2:2][CH2:3]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 70980010Ethyl 5-(cyclopropylcarbamoyl)isoxazole-3-carboxylate

Product 1

HCID 867146445-(Cyclopropylcarbamoyl)isoxazole-3-carboxylic acidYield 23.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ethyl 5-(cyclopropylcarbamoyl)isoxazole-3-carboxylate (1.267 mmol, 0.284 g) was dissolved in ethanol (10 ml). The mixture was cooled in an ice bath and NaOH 2 M solution (2.53 mmol, 1.267 ml) was added. The resulting mixture was stirred in cold until the reaction was complete. Ethanol was evaporated and water was added. The pH of the mixture was adjusted to 4 with HCl. The precipitate was removed by filtration. The filtrate was evaporated and purified by trituration from 1/9 MeOH/DCM. 0.058 g of the title compound was obtained. 1H-NMR (400 MHz, DMSO-d6): δ 0.57-0.66 (m, 2H), 0.67-0.75 (m, 2H), 2.77-2.88 (m, 1H), 6.97 (s, 1H), 8.85 (m, 1H).

Workup

  1. temperatureThe mixture was cooled in an ice bath
  2. customEthanol was evaporated
  3. additionwater was added
  4. customThe precipitate was removed by filtration
  5. customThe filtrate was evaporated
  6. custompurified by trituration from 1/9 MeOH/DCM

Sources & evidence

ORD record
ord-00dfd005e1c3499598309e740d97b4fb
Source dataset
uspto-grants-2014_12
Patent number
US08921378B2

Reaction notes

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