(3R,4S)-4-{4-[(E)-2-(2-aminophenylcarbamoyl)-vinyl]-phenyl}-1-methyl-pyrrolidine-3-carboxylic acid (4-chlorophenyl)amide

Base Information

• Chemical Name: (3R,4S)-4-{4-[(E)-2-(2-aminophenylcarbamoyl)-vinyl]-phenyl}-1-methyl-pyrrolidine-3-carboxylic acid (4-chlorophenyl)amide
• CAS No.: 1241918-69-3
• Molecular Formula: C₂₇H₂₇ClN₄O₂
• Molecular Weight: 474.99
• Mol file: 1241918-69-3.mol

Synonyms:(3R,4S)-4-{4-[(E)-2-(2-aminophenylcarbamoyl)-vinyl]-phenyl}-1-methyl-pyrrolidine-3-carboxylic acid (4-chlorophenyl)amide

Chemical Property of (3R,4S)-4-{4-[(E)-2-(2-aminophenylcarbamoyl)-vinyl]-phenyl}-1-methyl-pyrrolidine-3-carboxylic acid (4-chlorophenyl)amide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3R,4S)-4-{4-[(E)-2-(2-aminophenylcarbamoyl)-vinyl]-phenyl}-1-methyl-pyrrolidine-3-carboxylic acid (4-chlorophenyl)amide

There total 12 articles about (3R,4S)-4-{4-[(E)-2-(2-aminophenylcarbamoyl)-vinyl]-phenyl}-1-methyl-pyrrolidine-3-carboxylic acid (4-chlorophenyl)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: 65.5%

[2-((E)-3-{4-[(3S,4R)-4-(4-chlorophenylcarbamoyl)-1-methyl-pyrrolidin-3-yl]-phenyl}-acryloylamino)-phenyl]-carbamic acid tert-butyl ester → (3R,4S)-4-{4-[(E)-2-(2-aminophenylcarbamoyl)-vinyl]-phenyl}-1-methyl-pyrrolidine-3-carboxylic acid (4-chlorophenyl)amide (1241918-69-3)

Guidance literature:

With hydrogenchloride; In methanol; at 0 - 5 ℃; for 4h; Large scale;

DOI:10.1021/op500250b

Reference yield:

N-(2-(acryloylamino)phenyl)carbamic acid tert-butyl ester (503039-31-4) → (3R,4S)-4-{4-[(E)-2-(2-aminophenylcarbamoyl)-vinyl]-phenyl}-1-methyl-pyrrolidine-3-carboxylic acid (4-chlorophenyl)amide (1241918-69-3)

Guidance literature:

Multi-step reaction with 4 steps

1.1: tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; tris-(o-tolyl)phosphine; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 5 h / 105 - 110 °C / Large scale

2.1: lithium hydroxide monohydrate / methanol; water / 2 h / 10 - 30 °C / Large scale

3.1: triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / tetrahydrofuran; dichloromethane / 0.33 h / 20 - 23 °C

3.2: 20 - 23 °C

4.1: hydrogenchloride / methanol / 4 h / 0 - 5 °C / Large scale

With hydrogenchloride; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; lithium hydroxide monohydrate; triethylamine; N-ethyl-N,N-diisopropylamine; tris-(o-tolyl)phosphine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; 1.1: |Heck Reaction;

DOI:10.1021/op500250b

Reference yield:

(3R,4S)-4-{4-[(E)-2-(2-tert-butoxycarbonylamino-phenylcarbamoyl)-vinyl]-phenyl}-1-methyl-pyrrolidine-3-carboxylic acid ethyl ester → (3R,4S)-4-{4-[(E)-2-(2-aminophenylcarbamoyl)-vinyl]-phenyl}-1-methyl-pyrrolidine-3-carboxylic acid (4-chlorophenyl)amide (1241918-69-3)

Guidance literature:

Multi-step reaction with 3 steps

1.1: lithium hydroxide monohydrate / methanol; water / 2 h / 10 - 30 °C / Large scale

2.1: triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / tetrahydrofuran; dichloromethane / 0.33 h / 20 - 23 °C

2.2: 20 - 23 °C

3.1: hydrogenchloride / methanol / 4 h / 0 - 5 °C / Large scale

With hydrogenchloride; lithium hydroxide monohydrate; triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In tetrahydrofuran; methanol; dichloromethane; water;

DOI:10.1021/op500250b

upstream raw materials:

1,2-diamino-benzene

N-(2-(acryloylamino)phenyl)carbamic acid tert-butyl ester

tert–butyl (2–aminophenyl)carbamate

4-bromo-benzaldehyde