Methyl isoxazole-5-carboxylate

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Methyl isoxazole-5-carboxylate Basic information
Product Name:Methyl isoxazole-5-carboxylate
Synonyms:AKOS PAO-1372;ISOXAZOLE-5-CARBOXYLIC ACID METHYL ESTER;Isoxazole-5-carboxylic acid ethyl ester;5-Isoxazolecarboxylic acid, Methyl ester;Methyl 1,2-oxazole-5-carboxylate, 5-(Methoxycarbonyl)isozazole;methyl 1,2-oxazole-5-carboxylate;methyl 5-isoxazolcarboxylate;methyl isoxazole-5-carboxylate - [M83091]
CAS:15055-81-9
MF:C5H5NO3
MW:127.1
EINECS:
Product Categories:
Mol File:15055-81-9.mol
Methyl isoxazole-5-carboxylate Structure
Methyl isoxazole-5-carboxylate Chemical Properties
Melting point 48-51
Boiling point 203.9±13.0 °C(Predicted)
density 1.229±0.06 g/cm3(Predicted)
storage temp. Store at room temperature
pka-3.88±0.50(Predicted)
AppearanceOff-white to light brown Solid
Safety Information
Hazard Codes Xi
Safety Statements 22-24/25
Hazard Note Irritant
HS Code 2934999090
MSDS Information
ProviderLanguage
ALFA English
Methyl isoxazole-5-carboxylate Usage And Synthesis
Uses5-Isoxazolecarboxylic Acid Methyl Ester is used as a reagent in the synthesis of pyridine derivatives as integrase inhibitors and antiviral agents. 5-Isoxazolecarboxylic Acid Methyl Ester is also a useful synthetic intermediate in the preparation of pyrazolopyrimidine derivatives useful in the prevention and treatment of cancer.
Synthesis
ISOXAZOLE-5-CARBOXYLIC ACID

21169-71-1

Iodomethane

74-88-4

METHYL ISOXAZOLE-5-CARBOXYLATE

15055-81-9

A mixture of isoxazole-5-carboxylic acid (2.5 g, 22.1 mmol), sodium bicarbonate (5.57 g, 66.32 mmol) and iodomethane (8.26 mL, 132.65 mmol) in N,N-dimethylformamide (DMF, 30 mL) was stirred and reacted for 19 hr at 25 °C. After completion of the reaction, the mixture was diluted with deionized water (30 mL) and extracted with ether (2 × 50 mL). The combined organic layers were washed with saturated saline, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure to give the crude product. The crude product was purified by a Biotage fast chromatography system (40 m column) with the eluent of ethyl acetate-hexane (1:2, v/v), followed by switching to pure ethyl acetate, resulting in methyl isoxazole-5-carboxylate as an amorphous solid (1.2 g, 42.7% yield). Mass spectrum (+ESI): m/z 128 [M+H]+.

References[1] Patent: US2007/219186, 2007, A1. Location in patent: Page/Page column 51
Methyl isoxazole-5-carboxylate Preparation Products And Raw materials
Raw materialsMethanol-->Isoxazole-5-carboxylic acid-->Iodomethane-->N,N-Dimethylformamide-->Sodium bicarbonate
Preparation Products5-Formylisoxazole
Tag:Methyl isoxazole-5-carboxylate(15055-81-9) Related Product Information
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