(3S,5S)-1-(tert-butoxy carbonyl)-5-(methoxy carbonyl)pyrrolidine-3 -carboxylic acid

Base Information

• Chemical Name: (3S,5S)-1-(tert-butoxy carbonyl)-5-(methoxy carbonyl)pyrrolidine-3 -carboxylic acid
• CAS No.: 1378388-35-2
• Molecular Formula: C12H19NO6
• Molecular Weight: 273.286
• Mol file: 1378388-35-2.mol

Synonyms:(3S,5S)-1-(tert-butoxy carbonyl)-5-(methoxy carbonyl)pyrrolidine-3 -carboxylic acid

Chemical Property of (3S,5S)-1-(tert-butoxy carbonyl)-5-(methoxy carbonyl)pyrrolidine-3 -carboxylic acid

Chemical Property:

• Boiling Point: 392.7±42.0 °C(Predicted)
• PKA: 4.19±0.40(Predicted)
• PSA: 93.14000
• Density: 1.260±0.06 g/cm3(Predicted)
• LogP: 0.80750

Purity/Quality:

98%,99%, ^*data from raw suppliers

(3S,5S)-5-methoxycarbonyl-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-3-carboxylicacid 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (3S,5S)-1-(tert-butoxy carbonyl)-5-(methoxy carbonyl)pyrrolidine-3 -carboxylic acid

There total 5 articles about (3S,5S)-1-(tert-butoxy carbonyl)-5-(methoxy carbonyl)pyrrolidine-3 -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: 70.0%

(2S,4S)-N-(tert-butyloxycarbonyl)pyrrolidine-2,4-dicarboxylic acid dimethyl ester (1378388-30-7) → (3S,5S)-N-(tert-butoxycarbonyl)-5-(methoxycarbonyl)-pyrrolidine-3-carboxylic acid (1378388-35-2)

Guidance literature:

With water; sodium hydroxide; In tert-Amyl alcohol; at 0 ℃; for 5.25h; Cooling with ice;

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) → (3S,5S)-N-(tert-butoxycarbonyl)-5-(methoxycarbonyl)-pyrrolidine-3-carboxylic acid (1378388-35-2)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium hydrogencarbonate / water; ethyl acetate / 12 h / 20 °C

2: sodium hydroxide / tetrahydrofuran; water / 5.25 h / 0 °C

With sodium hydrogencarbonate; sodium hydroxide; In tetrahydrofuran; water; ethyl acetate;

Reference yield:

(2S,4S)-4-cyano-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester (487048-28-2) → (3S,5S)-N-(tert-butoxycarbonyl)-5-(methoxycarbonyl)-pyrrolidine-3-carboxylic acid (1378388-35-2)

Guidance literature:

Multi-step reaction with 2 steps

1.1: hydrogenchloride / 1,4-dioxane / 16 h / 20 °C

1.2: 12 h / 20 °C

2.1: water; sodium hydroxide / tert-Amyl alcohol / 5.25 h / 0 °C / Cooling with ice

With hydrogenchloride; water; sodium hydroxide; In 1,4-dioxane; tert-Amyl alcohol;

upstream raw materials:

(2S,4S)-4-cyano-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester

(2S,4S)-N-(tert-butyloxycarbonyl)pyrrolidine-2,4-dicarboxylic acid dimethyl ester

di-tert-butyl dicarbonate

(2S,4S)-pyrrolidine-2,4-dicarboxylic acid dimethyl ester

Downstream raw materials:

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

(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

tert-butyl (2S,4S)-2-[5-(2-{(2S,5S)-1-[N-(methoxycarbonyl)-L-valyl]-5-methylpyrrolidin-2-yl}-1,4,5,11-tetrahydroisochromeno[4′,3′:6,7]naphtho[1,2-d]imidazol-9-yl)-1H-imidazol-2-yl]-4-(methoxymethyl)pyrrolidine-1-carboxylate

tert-butyl (2S,4S)-2-[5-(2-{(2S,5S)-1-[N-(methoxycarbonyl)-L-valyl]-5-methylpyrrolidin-2-yl}-1,11-dihydroisochromeno[4′,3′:6,7]naphtho[1,2-d]imidazol-9-yl)-1H-imidazol-2-yl]-4-(methoxymethyl)pyrrolidine-1-carboxylate

Refernces

• 1、 -. "Deuterated antiviral active compounds for hepatitis C viruses". Paragraph 0017; 0018; 0021. . Retrieved 2018/04/01.
• 2、 -. "PROCESSES FOR PREPARING ANTIVIRAL COMPOUNDS". Paragraph 0400. . Retrieved 2015/12/30.