| Identification | Back Directory | [Name]
(2S,5S)-1-((methoxycarbonyl)-L-valyl)-5-methylpyrrolidine-2-carboxylic acid | [CAS]
1335316-40-9 | [Synonyms]
PLV-09-40
Velpatasvir Impurity 6
Velpatasvir Intermediate 5
(2S,5S)-1-(2-Methoxycarbonylamino-
(5 S)-N-(methoxyl)- L- valanyl-5-methyl- L- proline
(5S)-N-(Methoxycarbonyl)-L-valyl-5-methyl-L-proline
(2S,5S)-1-((S)-2-(methoxycarbonyl)-3-methylbutanoyl)
L-Proline, N-(methoxycarbonyl)-L-valyl-5-methyl-, (5S)-
(5S)-N-(methoxycarbonyl) -L-valaminoyl-5-methyl-L-proline
(2S,5S)-1-((methoxycarbonyl)-L-valyl)-5-methylpyrrolidine-2-carboxylic
N-[2-(S)-[(Methoxycarbonyl)amino]-3-methylbutyryl]-(5S)-5-Methyl-L-proline
(2S,5S)-1-((methoxycarbonyl)-L-valyl)-5-methylpyrrolidine-2-carboxylic acid
(2S,5S)-1-(2-Methoxycarbonylamino-3-methyl-butyryl)-5-methyl-pyrrolidine-2-carboxylic acid
(2S,5S)-1-((S)-2-METHOXYCARBONYLAMINO)-3-METHYLBUTYRYL)-5-METHYLPYRROLIDINE-2-CARBOXYLIC ACID
(2R,5R)-1-((S)-2-(Methoxycarbonylamino)-3-methylbutanoyl)-5-methylpyrrolidine-2-carboxylic acid
(2S,5S)-1-((S)-2-((methoxycarbonyl)amino)-3-methylbutanoyl)-5-methylpyrrolidine-2-carboxylic acid
3. (2S,5S)-1-((S)-2-((methoxycarbonyl)amino)-3- methylbutanoyl)-5-methylpyrrolidine-2-carboxylic acid
(2S,4S)-1-((R)-2-((methoxycarbonyl)
amino)-2-phenylacetyl)-4-(methoxy
methyl)pyrrolidine-2-carboxylic acid | [EINECS(EC#)]
811-415-9 | [Molecular Formula]
C13H22N2O5 | [MDL Number]
MFCD29917577 | [MOL File]
1335316-40-9.mol | [Molecular Weight]
286.33 |
| Chemical Properties | Back Directory | [Melting point ]
134 - 136°C | [Boiling point ]
489.9±40.0 °C(Predicted) | [density ]
1.198±0.06 g/cm3(Predicted) | [storage temp. ]
-20°C, Inert atmosphere | [solubility ]
Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly) | [form ]
Solid | [pka]
3.61±0.40(Predicted) | [color ]
Off-White to Pale Beige | [InChI]
InChI=1S/C13H22N2O5/c1-7(2)10(14-13(19)20-4)11(16)15-8(3)5-6-9(15)12(17)18/h7-10H,5-6H2,1-4H3,(H,14,19)(H,17,18)/t8-,9-,10-/m0/s1 | [InChIKey]
PNAXKGVRCAXIJK-GUBZILKMSA-N | [SMILES]
C(O)(=O)[C@@H]1CC[C@H](C)N1C(=O)[C@H](C(C)C)NC(OC)=O |
| Hazard Information | Back Directory | [Uses]
(5S)-N-(Methoxycarbonyl)-L-valyl-5-methyl-L-proline is an antiviral agent and Velpatasvir (V116000) intermediate. Velpatasvir is a NS5A inhibitor in patients with hepatitis C (HCV) infection. | [Synthesis]
To an ice-cold stirred solution of ethyl (2S,5S)-1 -[(2S)-2- (methoxycarbonylamino)-3-methyl-butanoyl]-5-methyl-pyrrolidine-2- carboxylate (5.6 g, 17.8 mmol) in ethanol (18 ml) is added a solution of lithium hydroxide monohydrate (17.8 mL of 1.7 M, 30.3 mmol). The reaction mixture is stirred for 5 hours at rt. The reaction mixture is concentrated, diluted with water, washed with ether. The aqueous solution is acidified with aq. 1 N HCl, extracted with CH2CI2. The combined extracts are washed with brine, dried (Na2S04), concentrated to afford (2S,5S)-1 -[(2S)-2-(methoxycarbonylamino)-3- methyl-butanoyl]-5-methyl-pyrrolidine-2-carboxylic acid (5g, 94%) as a white solid. |
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