| Identification | More | [Name]
(R)-(-)-3-Carbamoymethyl-5-methylhexanoic acid | [CAS]
181289-33-8 | [Synonyms]
(r)-(-)-3-(2-amino-2-oxoethyl)-5-methylhexanoic acid
(r)-(-)-3-carbamoymethyl-5-methylhexanoic acid
INTERMEDIATE OF PREGABALIN
(R)-3-(2-AMINO-2-OXOETHYL)-5-METHYLHEXANOIC ACID:99+% | [EINECS(EC#)]
605-923-8 | [Molecular Formula]
C9H17NO3 | [MDL Number]
MFCD09028111 | [Molecular Weight]
187.236 | [MOL File]
181289-33-8.mol |
| Chemical Properties | Back Directory | [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 Rotation]
-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) |
| Questions And Answer | Back Directory | [Uses]
(R)-(-)-3-Carbamoymethyl-5-methylhexanoic acid is a useful chemical intermediate for manufacturing of the anticonvulsant drug, Pregabalin1, 2.
| [Sources]
- https://quod.lib.umich.edu/a/ark/5550190.0011.a22?rgn=main;view=fulltext
- https://www.researchgate.net/publication/269660675_Synthesis_and_characterization_of_impurities_of_an_anticonvulsant_drug_Pregabalin
|
| Hazard Information | Back Directory | [Chemical Properties]
White Solid | [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 |
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