Ethyl 1-aminocyclopropanecarboxylate hydrochloride Chemical Properties

Melting point:

gt. 110.0 and le 118.0 °C

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

Water Solubility 

Soluble in water

form 

Crystalline Powder

color 

White

CAS DataBase Reference

42303-42-4

Safety Information

Hazard Codes 

Xn

Risk Statements 

36/37/38-22

Safety Statements 

26-36-38-36/37-24/25-22-7/9-36/37/39

WGK Germany 

3

HS Code 

29224999

Ethyl 1-aminocyclopropanecarboxylate hydrochloride Usage And Synthesis

Chemical Properties

White crystalline powder

Uses

peptide synthesis

reaction suitability

reaction type: solution phase peptide synthesis

Synthesis

Thionyl chloride (150 mL, 2.056 mol) was slowly added to a suspension of 1-aminocyclopropanecarboxylic acid (100 g, 0.989 mol) in anhydrous ethanol (1 L) below 0 °C. The reaction mixture was stirred at 70 °C for 20 hours. The progress of the reaction was monitored by thin layer chromatography (TLC, unfolding agent: methanol, Rf = 0.4) to confirm that most of the raw materials had been consumed. Upon completion of the reaction, the solution was concentrated to give 210 g of crude product. The residue was dissolved in water and the pH was adjusted to 9-10 with potassium carbonate.Subsequently, the aqueous layer was extracted with dichloromethane (1L x 3). The organic layers were combined and concentrated to dryness. The residue was dissolved in ethyl acetate (300 mL) and a hydrochloride solution of ethyl hydrochloride (250 mL, 4 M) was slowly added at below -30°C. The mixture was stirred at 0 °C for 30 min, during which time a solid precipitated. Filtration under nitrogen protection gave ethyl 1-aminocyclopropane-1-carboxylate hydrochloride (132 g, 80.6% yield) as a white solid. The 1H-NMR data of the free amine were as follows (400 MHz, chloroform-d): δ[ppm] = 0.91-1.02 (m, 2H), 1.15-1.30 (m, 5H), 2.17 (s, 2H), 4.10 (d, 2H).

References

[1] Journal of Medicinal Chemistry, 1986, vol. 29, # 10, p. 1840 - 1846
[2] Patent: WO2014/147021, 2014, A2. Location in patent: Page/Page column 129
[3] Patent: WO2015/140195, 2015, A1. Location in patent: Page/Page column 92; 93
[4] Patent: US2006/25589, 2006, A1. Location in patent: Page/Page column 9

Ethyl 1-aminocyclopropanecarboxylate hydrochloride(42303-42-4)Related Product Information

• DL-HISTIDINE MONOHYDROCHLORIDE
• L(+)-Ornithine hydrochloride
• L-Arginine hydrochloride
• DL-Cysteine hydrochloride monohydrate
• 2-Amino-2-methyl-propionic acid ethyl ester hydrochloride
• ALPHA-AMINOISOBUTYRIC ACID METHYL ESTER HYDROCHLORIDE
• 1-AMINO-CYCLOPROPANEMETHANOL
• Ethyl 1-aminocyclopropanecarboxylate hydrochloride
• Cyclopropylamine
• 1-Aminocyclopropanecarboxylic acid
• Ethyl cyclopropanecarboxylate
• H-D-ALA-OET HCL
• Methyl 1-aminocyclopropanecarboxylate hydrochloride
• 2-AMINO-2-METHYL-1-PROPANOL HYDROCHLORIDE
• 1-Aminocyclopropane-1-carboxylic acid hydrochloride
• 1-METHYL-1-CYCLOPROPANAMINE
• Cyclopropanecarboxylic acid, 1-amino-2-ethenyl-, ethyl ester, hydrochloride (9CI)
• Cyclopropanecarboxylic acid, 1-amino-2-ethenyl-, ethyl ester, hydrochloride (1:1),(1R,2S)-rel-