Hydrochloric Acid → 3-(Methoxycarbonyl)amino-4-methoxy-isoxazole-5-carboxylic acid

HRID 6888Notes

Reaction equation

HRID 6888 reaction equation
C[O:2][C:3]([C:5]1[O:9][N:8]=[C:7]([NH:10][C:11]([O:13][CH3:14])=[O:12])[C:6]=1[O:15][CH3:16])=[O:4].[OH-].[Na+].Cl>O>[CH3:14][O:13][C:11]([NH:10][C:7]1[C:6]([O:15][CH3:16])=[C:5]([C:3]([OH:4])=[O:2])[O:9][N:8]=1)=[O:12]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 220192003-Carbomethoxyamino-4-methoxy-5-carbomethoxyisoxazol

Product 1

HCID 220192133-(Methoxycarbonyl)amino-4-methoxy-isoxazole-5-carboxylic acidYield 84,537.898%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 2.50 g (0.011 mmol) of methyl-3-(methoxycarbonyl)amino-4-methoxy-isoxazole-5-carboxylate (prepared according to the method described in W. Kloetzer, J. Schantz, Monatsh. Chem., 1965, 102–115) and 1.30 g of powdered sodium hydroxide dissolved in 9 ml of water is heated at 90° C. for 3 hours. After cooling, the mixture is acidified to pH=2 with concentrated hydrochloric acid, controlling the temperature so as not to exceed 5° C. After 1 hour of stirring at 0° C., the precipitate obtained is filtered off and washed with cold water. There is obtained 2.01 g (86% yield) of a white solid (M+1=217).

Workup

  1. customprepared
  2. temperatureAfter cooling
  3. customto exceed 5° C
  4. customthe precipitate obtained
  5. filtrationis filtered off
  6. washwashed with cold water

Sources & evidence

ORD record
ord-c6cbca41f26745508b2a75aeede61ad4
Source dataset
uspto-grants-2006_08
Patent number
US07084163B2

Reaction notes

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