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)

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 Information

WGK Germany 

WGK 3

HS Code 

2924.19.8000

Storage Class

11 - Combustible Solids

Hazard Classifications

Skin Irrit. 2

3-Carbamoymethyl-5-methylhexanoic acid Usage And Synthesis

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

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(181289-15-6)Related Product Information

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