(R)-(-)-3-Carbamoymethyl-5-methylhexanoic acid CAS#: 181289-33-8; ChemWhat Code: 1016635
Identification
| Product Name | (R)-(-)-3-Carbamoymethyl-5-methylhexanoic acid CAS#: 181289-33-8 |
| IUPAC Name | (3R)-3-(2-amino-2-oxoethyl)-5-methylhexanoic acid |
| Molecular Structure |  |
| CAS Registry Number | 181289-33-8 |
| EINECS Number | No data available |
| MDL Number | MFCD09028111 |
| Beilstein Registry Number | 11747721 |
| Synonyms | (R)-(-)-3-(carbamoylmethyl)-5-methylhexanoic acid(3R)-3-(carbamoylmethyl)-5-methylhexa |
| Molecular Formula | C9H17NO3 |
| Molecular Weight | 187.239 |
| 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 |
| InChI Key | NPDKTSLVWGFPQG-SSDOTTSWSA-N |
| Canonical SMILES | CC(C)CC@HCC(=O)O |
| Patent Information | ||
| Patent ID | Title | Publication Date |
| US2014/243412 | PROCESS FOR PREPARATION OF PREGABALIN | 2014 |
| US2007/293694 | Processes for the preparation of R-(+)-3-(carbamoyl methyl)-5-methylhexanoic acid and salts thereof | 2007 |
| US5616793 | PYRROLO[1,2-b]PYRIDAZINE DERIVATIVES | 1997 |
Physical Data
| Appearance | White powder |
| Solubility | No data available |
| Flash Point | No data available |
| Refractive index | No data available |
| Sensitivity | No data available |
| Melting Point, °C | Solvent (Melting Point) |
| 131 – 135 | diethyl ether |
| 105 – 106 | |
| 130 – 133 | |
| 132 – 135 | ethyl acetate |
| Chromatographic data | Original string |
| LC (Liquid chromatography) | |
| HPLC (High performance liquid chromatography) | Informative Retention time: R-Isomer:- ~ 12.7 min |
Spectra
| Description (NMR Spectroscopy) | Nucleus (NMR Spectroscopy) | Solvents (NMR Spectroscopy) | Frequency (NMR Spectroscopy), MHz | Original Text (NMR Spectroscopy) | Comment (NMR Spectroscopy) |
| Chemical shifts, Spectrum | 1H | dimethylsulfoxide-d6 | 300 | ||
| Chemical shifts, Spectrum | 13C | dimethylsulfoxide-d6 | 50 | ||
| 1H | dimethylsulfoxide-d6 | 400 | δH (400 MHz, DMSO-d6): 0.81 (app d, J 6.6, 6H), 1.09 (app t, J 6.6, 2H), 1.51-1.66 (m, 1 H), 1.91-2.22 (m, 5H), 6.74 (s, 1 H), 7.27 (s, 1 H), 12.0 (br s, 1 H). | Signals given | |
| 13C | dimethylsulfoxide-d6 | 100 | δc (100 MHz, DMSO-d6): 23.1 , 23.2, 25.0, 30.1 , 39.2, 40.2, 43.6, 173.8, 174.3. | Signals given |
| Description (IR Spectroscopy) | Solvent (IR Spectroscopy) | Original Text (IR Spectroscopy) |
| Bands | potassium bromide | |
| in KBr | CCl4 | IR (KBr) :3436.17, 1712.53, 1644.29 cm“1. |
| Description (Mass Spectrometry) |
| spectrum |
| tandem mass spectrometry, spectrum |
| ESI (Electrospray ionisation), HRMS (High resolution mass spectrometry) |
Route of Synthesis (ROS)
| Conditions | Yield |
| Stage #1: (3S)-3-(2-ethoxy-2-oxoethyl)-5-methylhexanoic acid With ammonium iodide; sodium amide In tetrahydrofuran at 20℃; for 4h; Cooling with ice; Green chemistry; Stage #2: With hydrogenchloride In water pH=4 – 5; Reagent/catalyst; Solvent; Green chemistry; | 86.7% |
| With ammonia; calcium chloride In methanol at 55 – 60℃; under 3000.3 – 3375.34 Torr; Autoclave; | |
| With ammonia; calcium chloride In methanol at 25 – 70℃; under 375.038 – 2250.23 Torr; Autoclave; |
Safety and Hazards
| Pictogram(s) |  |
| Signal | Warning |
| GHS Hazard Statements | H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral] H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation] H319 (100%): Causes serious eye irritation [Warning Serious eye damage/eye irritation] H335 (100%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation] Information may vary between notifications depending on impurities, additives, and other factors. |
| Precautionary Statement Codes | P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (The corresponding statement to each P-code can be found at the GHS Classification page.) |
Other Data
| Transportation | NONH for all modes of transport |
| Under the room temperature and away from light | |
| HS Code | No data available |
| Storage | Under the room temperature and away from light |
| Shelf Life | 1 year |
| Market Price | USD |
| Druglikeness | |
| Lipinski rules component | |
| Molecular Weight | 187.239 |
| logP | 1.074 |
| HBA | 4 |
| HBD | 2 |
| Matching Lipinski Rules | 4 |
| Veber rules component | |
| Polar Surface Area (PSA) | 80.39 |
| Rotatable Bond (RotB) | 6 |
| Matching Veber Rules | 2 |
| Use Pattern |
| Pharmaceuticals |
| pregabalin intermediate for treating anxiety |
| pregabalin intermediate for treating epilepsy |
| pregabalin intermediate for treating neuropathic pain |
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