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| | 1-Aminocyclobutanecarboxylic acid Basic information |
| | 1-Aminocyclobutanecarboxylic acid Chemical Properties |
| Melting point | 261 °C (dec.)(lit.) | | Boiling point | 241.1±23.0 °C(Predicted) | | density | 1.290±0.06 g/cm3(Predicted) | | storage temp. | Keep in dark place,Inert atmosphere,Room temperature | | pka | 2.38±0.20(Predicted) | | form | Powder | | color | White | | Water Solubility | Soluble to 100 mM in water. | | Major Application | peptide synthesis | | InChI | InChI=1S/C5H9NO2/c6-5(4(7)8)2-1-3-5/h1-3,6H2,(H,7,8) | | InChIKey | FVTVMQPGKVHSEY-UHFFFAOYSA-N | | SMILES | C1(N)(C(O)=O)CCC1 | | CAS DataBase Reference | 22264-50-2(CAS DataBase Reference) |
| Hazard Codes | Xn | | Risk Statements | 22-36/37/38 | | Safety Statements | 26-36 | | WGK Germany | 3 | | RTECS | GU1336000 | | HazardClass | IRRITANT | | HS Code | 2922498590 | | Storage Class | 11 - Combustible Solids | | Hazard Classifications | Acute Tox. 4 Oral
Eye Irrit. 2
Skin Irrit. 2
STOT SE 3 |
| | 1-Aminocyclobutanecarboxylic acid Usage And Synthesis |
| Uses | 1-Aminocyclobutanecarboxylic acid acts as an agonist being an analog of glycine at the NMDA-glycine receptor site. This affects the signal transmission in the CNS. | | Uses | ACBC is an NMDA receptor antagonist acting at the glycine site. It acts as an agonist being an analog of glycine at the NMDA-glycine receptor site. This affects the signal transmission in the CNS. | | Definition | ChEBI: 1-AMINOCYCLOBUTANE CARBOXYLIC ACID is a L-alpha-amino acid. | | reaction suitability | reaction type: solution phase peptide synthesis | | Biological Activity | NMDA receptor antagonist acting at the glycine site. | | Synthesis | 1. 1-carbamoyl-cyclobutanecarboxylic acid (1.43 g, 10.0 mmol, 1 eq.) was dissolved in a water-ice bath under nitrogen protection and 1N aqueous NaOH solution (10 mL, 10.0 mmol, 1 eq.) was added slowly.
2. NaOCl solution (10-13% solution, 9.0 mL, ~15.0 mmol, 1.5 eq.) was added slowly and the reaction mixture was stirred for 1 hour at 5 °C.
3. 10N NaOH solution (2.0 mL, 20 mmol, 2 eq.) was added slowly, keeping the reaction temperature below 20 °C and stirred at 15-25 °C for 3 h. The reaction was monitored by LC-MS. The completion of the reaction was monitored by LC-MS.
4. Quench the reaction with an aqueous solution (3 mL) of Na2S2O3-3H2O (2.48 g, 10 mmol, 1 eq.) at 15 °C and continue stirring for 1 hour.
5. Neutralize the reaction mixture with 12N HCl aqueous solution to pH=7.0.
6. Volatiles were removed by azeotropic distillation with toluene under reduced pressure to give about 9 g of white solid.
7. The solid was extracted with methanol (3 x 30 mL) and 2.0 g of crude product was obtained after evaporation of methanol.
8. By 1H NMR analysis, it was determined that the solid contained 0.81 g of the target product, 1-aminocyclobutanecarboxylic acid (70% yield), and the rest were inorganic salts.
9. Comparison of 1H and 13C NMR data confirmed that the structure of the product was consistent with the standard sample provided by Sumitomo Chemical, Inc. | | storage | Room temperature | | References | [1] Patent: WO2005/19158, 2005, A1. Location in patent: Page/Page column 18 |
| | 1-Aminocyclobutanecarboxylic acid Preparation Products And Raw materials |
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