1-(ethoxycarbonyl)cyclopropanecarboxylic acid

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1-(ethoxycarbonyl)cyclopropanecarboxylic acid manufacturers

1-(ethoxycarbonyl)cyclopropanecarboxylic acid Basic information
Product Name:1-(ethoxycarbonyl)cyclopropanecarboxylic acid
Synonyms:1-(ethoxycarbonyl)cyclopropanecarboxylic acid;2-METHYL-2-PROPANYL [(3R)-3-MORPHOLINYLMETHYL]CARBAMATE;1,1-Cyclopropanedicarboxylic acid, 1-ethyl ester;1-(Ethoxycarbonyl)Cyclopropanecarboxylic Acid(WXC03382);Cyclopropane-1,1-dicarboxylic acid ethyl ester;hoxycarbonyl)cyclopropanecarboxylic acid;Monoethyl 1,1-cyclopropanedicarboxylate;Ethyl cyclopropane-1,1-dicarboxylate
CAS:3697-66-3
MF:C7H10O4
MW:158.15
EINECS:
Product Categories:
Mol File:3697-66-3.mol
1-(ethoxycarbonyl)cyclopropanecarboxylic acid Structure
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
pka3.46±0.20(Predicted)
form liquid
color Clear, colourless
Safety Information
HS Code 2917200090
MSDS Information
1-(ethoxycarbonyl)cyclopropanecarboxylic acid Usage And Synthesis
Uses1-(Ethoxycarbonyl)cyclopropanecarboxylic Acid is used in preparation of broad-spectrum anticancer medicine cabozantinib.
Synthesis
Diethyl 1,1-cyclopropanedicarboxylate

1559-02-0

1-(ethoxycarbonyl)cyclopropanecarboxylic acid

3697-66-3

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: CN105111155, 2018, B. Location in patent: Paragraph 0038; 0051; 0055; 0056
[3] Patent: US2008/45556, 2008, A1. Location in patent: Page/Page column 21
[4] Patent: US2010/239576, 2010, A1
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