1-(ethoxycarbonyl)cyclopropanecarboxylic acid Chemical Properties

Boiling point:

66-69℃ (0.15 Torr)

Density 

1.339±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

pka

3.46±0.20(Predicted)

form 

liquid

color 

Clear, colourless

Safety Information

HS Code 

2917200090

1-(ethoxycarbonyl)cyclopropanecarboxylic acid Usage And Synthesis

Uses

1-(Ethoxycarbonyl)cyclopropanecarboxylic Acid is used in preparation of broad-spectrum anticancer medicine cabozantinib.

Synthesis

1-(Ethoxycarbonyl)cyclopropanecarboxylic acid was synthesized as follows: A solution of diethyl 1,1-cyclopropanedicarboxylate (20 g) in 1N NaOH (107 mL) and ethanol (220 mL) was hydrolyzed for 16 hours. Ethanol was removed by decompression distillation. The remaining starting material was extracted with ethyl acetate. The aqueous layer was acidified with 1N HCl. The reaction mixture was then extracted with ethyl acetate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography to afford 1-(ethoxycarbonyl)cyclopropanecarboxylic acid in 94% yield. 1H NMR (CDCl3) δ 1.06 (t, 3H), 1.53 (m, 2H), 1.62 (m, 2H), 4.21 (q, 2H). ESI-MS: m/z 159 [M+H]+ for C7H10O4.

References

[1] Patent: WO2005/79812, 2005, A1. Location in patent: Page/Page column 45-46
[2] Patent: WO2005/79812, 2005, A1. Location in patent: Page/Page column 45-46
[3] Patent: CN105111155, 2018, B. Location in patent: Paragraph 0038; 0051; 0055; 0056
[4] Patent: US2008/45556, 2008, A1. Location in patent: Page/Page column 21
[5] Patent: US2010/239576, 2010, A1

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