3-Carbamoymethyl-5-methylhexanoic acid CAS 181289-15-6
3-Carbamoymethyl-5-methylhexanoic acid Basic informationPhysical Form Uses
| Product Name: | 3-Carbamoymethyl-5-methylhexanoic acid |
| Synonyms: | 3-Carbamoymethyl-5-methylhexanoic acid;3-Carbamoymethyl-5-methylhexanoic acid (Pregabalin);3-(2-Amino-2-oxoethyl)-5-methylhexanoic acid;()-3-(AMIOMETHYL)-5-METHYLHEXANOIC ACID;3-Carbamoymethyl-5-m;3-(Carbamoylmethyi-5-methyl hexanoic acid;(2-aMino-2-oxoethyl)-5-Methylhexanoic acid;Pregabalin intermediate |
| CAS: | 181289-15-6 |
| MF: | C9H17NO3 |
| MW: | 187.24 |
| EINECS: | 605-922-2 |
| Product Categories: | APIs Intermediate;intermidiate of Pregablin;Pharmaceutical material and intermeidates |
| Mol File: | 181289-15-6.mol |
3-Carbamoymethyl-5-methylhexanoic acid Chemical Properties
| Melting point | 106-108°C |
| Boiling point | 401.9±28.0 °C(Predicted) |
| density | 1.080±0.06 g/cm3(Predicted) |
| storage temp. | Sealed in dry,Room Temperature |
| solubility | DMSO (Slightly), Methanol (Slightly), Water (Slightly) |
| pka | 4.68±0.10(Predicted) |
| form | Solid |
| color | White to Off-White |
| Major Application | pharmaceutical small molecule |
| InChI | InChI=1S/C9H17NO3/c1-6(2)3-7(4-8(10)11)5-9(12)13/h6-7H,3-5H2,1-2H3,(H2,10,11)(H,12,13) |
| InChIKey | NPDKTSLVWGFPQG-UHFFFAOYSA-N |
| SMILES | C(O)(=O)CC(CC(N)=O)CC(C)C |
| CAS DataBase Reference | 181289-15-6(CAS DataBase Reference) |
Safety Information
| WGK Germany | WGK 3 |
| HS Code | 2924.19.8000 |
| Storage Class | 11 - Combustible Solids |
| Hazard Classifications | Skin Irrit. 2 |
| Physical Form | Powder |
| Uses | 3-(2-Amino-2-oxoethyl)-5-methylhexanoic Acid is a Pregabalin, a GABA analogue used as an anticonvulsant, intermediate. |
| Uses | 3-?(2-?Amino-?2-?oxoethyl)?-?5-?methylhexanoic Acid is a Pregabalin (P704800), a GABA analogue used as an anticonvulsant, intermediate. |
| Synthesis | 185815-59-2 181289-15-6 The general procedure for the synthesis of 3-(aminocarbonylmethyl)-5-methylhexanoic acid using 4-isobutyldihydro-2H-pyran-2,6(3H)-dione as a starting material was as follows: first, 70 g of the dried product of 3-isobutylglutaric acid was reacted with 70 g of acetic anhydride at 120 °C for 2 h to produce 3-isobutylglutaric anhydride. Subsequently, 75g of 3-isobutylglutaric anhydride solution was slowly added dropwise to 180g of ammonia, and the temperature was controlled at 10°C during the reaction. After the dropwise addition, the reaction was continued for 2 hours. After the completion of the reaction, the pH of the solution was adjusted to 2~3 with hydrochloric acid, and a white powdery solid was obtained by filtration, i.e., the target product 3-isobutylglutaric acid monoamide. Liquid phase detection of the product showed a purity of 99.8%, a yield of 95% and an overall yield of 77.5%. Figure 4 illustrates the liquid phase assay results of 3-isobutylglutaric acid monoamide. |
| References | [1] Patent: CN106278931, 2017, A. Location in patent: Paragraph 0038; 0039; 0040 [2] Patent: WO2012/93411, 2012, A2. Location in patent: Page/Page column 18-19 [3] Patent: WO2009/4643, 2009, A2. Location in patent: Page/Page column 26 [4] Organic Process Research and Development, 2009, vol. 13, # 4, p. 812 - 814 |
3-Carbamoymethyl-5-methylhexanoic acid Preparation Products And Raw materials
| Raw materials | 3-isobutylglutaric acid-->Pentanedioic acid, 3-(2-methylpropyl)-, 1-[1-(1-naphthalenyl)ethyl] ester-->3-isobutylglutaric anhydride |
| Preparation Products | Hexanoicacid, 3-(2-amino-2-oxoethyl)-5-methyl-, (3S)--->(R)-(-)-3-Carbamoymethyl-5-methylhexanoic acid |
