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

Base Information

• Chemical Name: (2S,5S)-1-((methoxycarbonyl)-L-valyl)-5-methylpyrrolidine-2-carboxylic acid
• CAS No.: 1335316-40-9
• Molecular Formula: C13H22N2O5
• Molecular Weight: 286.328
• Mol file: 1335316-40-9.mol

Synonyms:(2S,5S)-1-((methoxycarbonyl)-L-valyl)-5-methylpyrrolidine-2-carboxylic acid;(2S,4S)-1-((R)-2-((methoxycarbonyl) amino)-2-phenylacetyl)-4-(methoxy methyl)pyrrolidine-2-carboxylic acid;(5S)-N-(Methoxycarbonyl)-L-valyl-5-methyl-L-proline;(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,5S)-1-((S)-2-(methoxycarbonyl)-3-methylbutanoyl);(2S,5S)-1-(2-Methoxycarbonylamino-3-methyl-butyryl)-5-methyl-pyrrolidine-2-carboxylic acid

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

Chemical Property:

• Boiling Point: 489.9±40.0 °C(Predicted)
• PKA: 3.61±0.40(Predicted)
• PSA: 95.94000
• Density: 1.198±0.06 g/cm3(Predicted)
• LogP: 1.15990
• Storage Temp.: -20°C, Inert atmosphere
• Solubility.: Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)

Purity/Quality:

98%, ^*data from raw suppliers

(5S)-N-(Methoxycarbonyl)-L-valyl-5-methyl-L-proline ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• 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.

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

There total 10 articles about (2S,5S)-1-((methoxycarbonyl)-L-valyl)-5-methylpyrrolidine-2-carboxylic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 94.0%

(2S,5S)-ethyl 1-((S)-2-(methoxycarbonylamino)-3-methylbutanoyl)-5-methylpyrrolidine-2-carboxylate (1335316-39-6) → (2S,5S)-1-((S)-2-(methoxycarbonylamino)-3-methylbutanoyl)-5-methylpyrrolidine-2-carboxylic acid (1335316-40-9)

Guidance literature:

(2S,5S)-ethyl 1-((S)-2-(methoxycarbonylamino)-3-methylbutanoyl)-5-methylpyrrolidine-2-carboxylate; With lithium hydroxide monohydrate; In ethanol; at 20 ℃; for 5h; Cooling with ice;

With hydrogenchloride; In water;

Reference yield: 94.0%

N-methoxycarbonyl-L-valine (111398-44-8,74761-42-5) + (2S,5S)-5-methylpyrrolidine-2-carboxylic acid ethyl ester (676560-84-2,166941-67-9) → (2S,5S)-1-((S)-2-(methoxycarbonylamino)-3-methylbutanoyl)-5-methylpyrrolidine-2-carboxylic acid (1335316-40-9)

Guidance literature:

N-methoxycarbonyl-L-valine; (2S,5S)-5-methylpyrrolidine-2-carboxylic acid ethyl ester; With N-ethyl-N,N-diisopropylamine; HATU; In N,N-dimethyl-formamide; at 0 - 20 ℃; for 20h;

With lithium hydroxide; In ethanol; water; at 20 ℃; for 5h; Cooling with ice;

Reference yield:

N-methoxycarbonyl-L-valine (111398-44-8,74761-42-5) → (2S,5S)-1-((S)-2-(methoxycarbonylamino)-3-methylbutanoyl)-5-methylpyrrolidine-2-carboxylic acid (1335316-40-9)

Guidance literature:

Multi-step reaction with 2 steps

1: N-ethyl-N,N-diisopropylamine; HATU / N,N-dimethyl-formamide / 20 h / 0 - 20 °C

2: lithium hydroxide monohydrate / ethanol / 5 h / 20 °C / Cooling with ice

With lithium hydroxide monohydrate; N-ethyl-N,N-diisopropylamine; HATU; In ethanol; N,N-dimethyl-formamide;

upstream raw materials:

N-methoxycarbonyl-L-valine

L-valine

(2S,5S)-ethyl 5-methylpyrrolidine-2-carboxylate 2,2,2-trifluoro acetate salt

(2S,5S)-ethyl 1-((S)-2-(methoxycarbonylamino)-3-methylbutanoyl)-5-methylpyrrolidine-2-carboxylate

Downstream raw materials:

tert-butyl (2S,5S)-2-[4-[4-[4-[2-[(2S,5S)-1-[2-(methoxycarbonylamino)-3-methyl-butanoyl]-5-methyl-pyrrolidin-2-yl]-1H-benzimidazol-5-yl]phenyl]phenyl]-1H-imidazol-2-yl]-5-methyl-pyrrolidine-1-carboxylate

methyl N-[2-methyl-1-[(2S,5S)-2-methyl-5-[4-[4-[4-[2-[(2S,5S)-5-methylpyrrolidin-2-yl]-1H-imidazol-5-yl]phenyl]phenyl]-1H-benzimidazol-2-yl]pyrrolidine-1-carbonyl]propyl]-carbamate

methyl N-[(1S)-1-[(2S,5S)-2-[4-[4-[4-[2-[(2S,5S)-1-[2-(methoxycarbonylamino)-3-methyl-butanoyl]-5-methyl-pyrrolidin-2-yl]-1H-benzimidazol-5-yl]phenyl]phenyl]-1H-imidazol-2-yl]-5-methyl-pyrrolidine-1-carbonyl]-2-methyl-propyl]carbamate

(2R,4R)-1-tert-butyl 2-(2-(9-((2S,5S)-1-((S)-2-(methoxycarbonylamino)-3-methylbutanoyl)-5-methylpyrrolidine-2-carbonyloxy)-8-oxo-8,9,10,11-tetrahydro-5H-dibenzo[c,g]chromen-3-yl)-2-oxoethyl) 4-(methoxymethyl)pyrrolidine-1,2-dicarboxylate