| Identification | More | [Name]
3-Carbamoymethyl-5-methylhexanoic acid | [CAS]
181289-15-6 | [Synonyms]
3-(2-Amino-2-oxoethyl)-5-methylhexanoic acid
3-Carbamoymethyl-5-methylhexanoic acid
3-Carbamoymethyl-5-methylhexanoic acid (Pregabalin)
()-3-(AMIOMETHYL)-5-METHYLHEXANOIC ACID | [EINECS(EC#)]
605-922-2 | [Molecular Formula]
C9H17NO4 | [MDL Number]
MFCD08457698 | [Molecular Weight]
203.24 | [MOL File]
181289-15-6.mol |
| Questions And Answer | Back Directory | [Physical Form]
Powder | [Uses]
3-(2-Amino-2-oxoethyl)-5-methylhexanoic Acid is a Pregabalin, a GABA analogue used as an anticonvulsant, intermediate. |
| Chemical Properties | Back Directory | [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) | [form ]
Solid | [pka]
4.68±0.10(Predicted) | [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 Data | Back Directory | [WGK Germany ]
WGK 3 | [HS Code ]
2924.19.8000 | [Storage Class]
11 - Combustible Solids | [Hazard Classifications]
Skin Irrit. 2 |
| Hazard Information | Back Directory | [Synthesis]
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 |
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