(2R,3R,4R,5S)-3-(3-chlorophenyl)-4-(4-chlorophenyl)-4-cyano-5-(2,2-dimethylpropyl)pyrrolidine-2-carboxylic acid ((S)-3,4-dihydroxybutyl)amide

Base Information

• Chemical Name: (2R,3R,4R,5S)-3-(3-chlorophenyl)-4-(4-chlorophenyl)-4-cyano-5-(2,2-dimethylpropyl)pyrrolidine-2-carboxylic acid ((S)-3,4-dihydroxybutyl)amide
• CAS No.: 1219082-06-0
• Molecular Formula: C₂₇H₃₃Cl₂N₃O₃
• Molecular Weight: 518.483

Synonyms:(2R,3R,4R,5S)-3-(3-chlorophenyl)-4-(4-chlorophenyl)-4-cyano-5-(2,2-dimethylpropyl)pyrrolidine-2-carboxylic acid ((S)-3,4-dihydroxybutyl)amide

Chemical Property of (2R,3R,4R,5S)-3-(3-chlorophenyl)-4-(4-chlorophenyl)-4-cyano-5-(2,2-dimethylpropyl)pyrrolidine-2-carboxylic acid ((S)-3,4-dihydroxybutyl)amide

Chemical Property:

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Technology Process of (2R,3R,4R,5S)-3-(3-chlorophenyl)-4-(4-chlorophenyl)-4-cyano-5-(2,2-dimethylpropyl)pyrrolidine-2-carboxylic acid ((S)-3,4-dihydroxybutyl)amide

There total 3 articles about (2R,3R,4R,5S)-3-(3-chlorophenyl)-4-(4-chlorophenyl)-4-cyano-5-(2,2-dimethylpropyl)pyrrolidine-2-carboxylic acid ((S)-3,4-dihydroxybutyl)amide 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: 34.4%

(2RS,3RS,4RS,5SR)-3-(3-chloro-phenyl)-4-(4-chloro-phenyl)-4-cyano-5-(2,2-dimethyl-propyl)-pyrrolidine-2-carboxylic acid ((S)-3,4-dihydroxy-butyl)-amide → (2S,3S,4S,5R)-3-(3-chlorophenyl)-4-(4-chlorophenyl)-4-cyano-5-(2,2-dimethylpropyl)pyrrolidine-2-carboxylic acid ((S)-3,4-dihydroxybutyl)amide (1219082-07-1) + (2R,3R,4R,5S)-3-(3-chlorophenyl)-4-(4-chlorophenyl)-4-cyano-5-(2,2-dimethylpropyl)pyrrolidine-2-carboxylic acid ((S)-3,4-dihydroxybutyl)amide (1219082-06-0)

Guidance literature:

With SFC chiral column; Resolution of racemate;

Reference yield:

(S)-2-(2,2-dimethyl-1,3-dioxolan-4-yl)ethan-1-amine (1008526-48-4) + racemic (2R,3R,4R,5S)-3-(3-chlorophenyl)-4-(4-chlorophenyl)-4-cyano-5-(2,2-dimethylpropyl)pyrrolidine-2-carboxylic acid trifluoroacetic acid salt → (2S,3S,4S,5R)-3-(3-chlorophenyl)-4-(4-chlorophenyl)-4-cyano-5-(2,2-dimethylpropyl)pyrrolidine-2-carboxylic acid ((S)-3,4-dihydroxybutyl)amide (1219082-07-1) + (2R,3R,4R,5S)-3-(3-chlorophenyl)-4-(4-chlorophenyl)-4-cyano-5-(2,2-dimethylpropyl)pyrrolidine-2-carboxylic acid ((S)-3,4-dihydroxybutyl)amide (1219082-06-0)

Guidance literature:

(S)-2-(2,2-dimethyl-1,3-dioxolan-4-yl)ethan-1-amine; racemic (2R,3R,4R,5S)-3-(3-chlorophenyl)-4-(4-chlorophenyl)-4-cyano-5-(2,2-dimethylpropyl)pyrrolidine-2-carboxylic acid trifluoroacetic acid salt; With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In dichloromethane; at 20 ℃; for 1h;

With pyridinium p-toluenesulfonate; In methanol; at 120 ℃; for 0.0833333h; Microwave irradiation;

DOI:10.1021/jm400487c

Reference yield:

3,3-dimethylbutyrylaldehyde (2987-16-8) → (2S,3S,4S,5R)-3-(3-chlorophenyl)-4-(4-chlorophenyl)-4-cyano-5-(2,2-dimethylpropyl)pyrrolidine-2-carboxylic acid ((S)-3,4-dihydroxybutyl)amide (1219082-07-1) + (2R,3R,4R,5S)-3-(3-chlorophenyl)-4-(4-chlorophenyl)-4-cyano-5-(2,2-dimethylpropyl)pyrrolidine-2-carboxylic acid ((S)-3,4-dihydroxybutyl)amide (1219082-06-0)

Guidance literature:

Multi-step reaction with 4 steps

1.1: dichloromethane / 20 °C

2.1: triethylamine; silver fluoride / dichloromethane / 18 h / 20 °C

3.1: dichloromethane / 18 h / 20 °C

4.1: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / dichloromethane / 1 h / 20 °C

4.2: 0.08 h / 120 °C / Microwave irradiation

With silver fluoride; triethylamine; N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In dichloromethane;

DOI:10.1021/jm400487c

upstream raw materials:

(S)-2-(2,2-dimethyl-1,3-dioxolan-4-yl)ethan-1-amine

3,3-dimethylbutyrylaldehyde

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