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

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

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

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.

(2S,5S)-1-((methoxycarbonyl)-L-valyl)-5-methylpyrrolidine-2-carboxylic acid(1335316-40-9)Related Product Information

• (1R,2R)-2-(3,4-difluorophenyl)cyclopropanecarboxylic acid
• Cyclopropanamine,2-(3,4-difluorophenyl)-(1R,2S) -(2R,3R)-2,3-dihydroxybutanedioate (1:1)
• 9-Bromo-3-(2-Bromo Acetyl)-10,11-Dihydro-5H-dibenzo(c,g) Chromen-8(9H)-one
• Aprepitant
• (2S,4S)-1-(tert-butoxycarbonyl)-4-(MethoxyMethyl)pyrrolidine-2-carboxylic acid
• N-BOC-CIS-4-CYANO-L-PROLINE METHYL ESTER
• Velpatasvir intermediate
• Velpatasvir
• Velpatasvir intermediate
• Velpatasvir intermediate
• (R)-2-(methoxycarbonylamino)-2-phenylacetic acid
• Velpatasvir Co Povidone
• Velpatasvir intermediate
• BOC-L-PYROGLUTAMIC ACID BENZYL ESTER
• Velpatasvir-A12
• 3-(2-bromoacetyl)-10,11-dihydro-5H-Benzo[d]naphtho[2,3-b]pyran-8(9H)-one
• Velpatasvir intermediate -II-RS isomer
• (2S,4R)-4-(Methoxymethyl)-1,2-pyrrolidinedicarboxylic Acid 1-(1,1-Dimethylethyl) Ester