(2S,5S)-1-((methoxycarbonyl)-L-valyl)-5-methylpyrrolidine-2-carboxylic acid

CAS NO.：1335316-40-9
Empirical Formula: C13H22N2O5
Molecular Weight: 286.32
MDL number: MFCD29917577
EINECS: 811-415-9
SAFETY DATA SHEET (SDS)
Update Date: 2024-09-02 10:48:58

What is (2S,5S)-1-((methoxycarbonyl)-L-valyl)-5-methylpyrrolidine-2-carboxylic acid?

The Uses of (2S,5S)-1-((methoxycarbonyl)-L-valyl)-5-methylpyrrolidine-2-carboxylic acid

(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.

Properties of (2S,5S)-1-((methoxycarbonyl)-L-valyl)-5-methylpyrrolidine-2-carboxylic acid

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

Safety information for (2S,5S)-1-((methoxycarbonyl)-L-valyl)-5-methylpyrrolidine-2-carboxylic acid

Computed Descriptors for (2S,5S)-1-((methoxycarbonyl)-L-valyl)-5-methylpyrrolidine-2-carboxylic acid

InChIKey	PNAXKGVRCAXIJK-GUBZILKMSA-N
SMILES	C(O)(=O)[C@@H]1CC[C@H](C)N1C(=O)[C@H](C(C)C)NC(OC)=O

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