(R)-(-)-3-Carbamoymethyl-5-methylhexanoic acid Chemical Properties

Melting point:

128-133°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)

form 

Solid

pka

4.68±0.10(Predicted)

color 

White to Off-White

optical activity

-6.5461°(C=1.0048g/100ml DMF)

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)/t7-/m1/s1

InChIKey

NPDKTSLVWGFPQG-SSDOTTSWSA-N

SMILES

C(O)(=O)C[C@@H](CC(N)=O)CC(C)C

CAS DataBase Reference

181289-33-8(CAS DataBase Reference)

(R)-(-)-3-Carbamoymethyl-5-methylhexanoic acid Usage And Synthesis

Uses

(R)-(-)-3-Carbamoymethyl-5-methylhexanoic acid is a useful chemical intermediate for manufacturing of the anticonvulsant drug, Pregabalin^{1, 2}.

Sources

1. https://quod.lib.umich.edu/a/ark/5550190.0011.a22?rgn=main;view=fulltext
2. https://www.researchgate.net/publication/269660675_Synthesis_and_characterization_of_impurities_of_an_anticonvulsant_drug_Pregabalin

Chemical Properties

White Solid

Uses

An Impurity of the anti-convulsant (S)-Pregabalin (P704790).

Synthesis

The general procedure for the synthesis of (R)-(-)-3-(aminocarbonylmethyl)-5-methylhexanoic acid from the compound (CAS:1385049-51-3) is as follows: Example 10f1: Synthesis of (R)-(-)-3-(carbamoylmethyl)-5-methylhexanoic acid 1. ammonia (116 ml) was added to the diastereomeric salt (14.5 g) and the mixture was heated to 80 °C at room temperature. 2. After maintaining the reaction at this temperature for 5 hours, the reaction mixture was cooled to room temperature. 3. The reaction mixture was extracted using dichloromethane (5 x 50 ml). 4. The aqueous layer was cooled to 0 °C and acidified to pH 1 with concentrated hydrochloric acid. 5. The acidified aqueous layer was extracted using hot ethyl acetate (5 x 50 ml). 6. All organic extracts were combined and concentrated under reduced pressure to give enantiomerically enriched amide I as a white solid. Yield: 8 g, 53% yield; HPLC purity: 99.39%.

References

[1] Patent: WO2012/93411, 2012, A2. Location in patent: Page/Page column 23

(R)-(-)-3-Carbamoymethyl-5-methylhexanoic acid(181289-33-8)Related Product Information

• EPA
• EC 2.3.2.2
• ALTRENOGEST
• Hexamethylphosphoramide
• Ethyl 2-(Chlorosulfonyl)acetate
• Ethyl Hexanoate
• Phenylmethylsulfonyl fluoride
• Folic acid
• Glycine
• 3-(Aminomethyl)-5-methylhexanoic acid
• 3-(Aminomethyl)-5-methylhexanoic acid
• Dimethyl sulfone
• 6-Aminocaproic acid
• Tris(hydroxymethyl)aminomethane
• Citric acid
• Ascoric Acid
• 2-Hexenamide, 2-cyano-5-methyl-
• Hexanoic acid,3-(aminomethyl)-5-methyl-, (3R)-