(1S,5R)-2-ethyl 1-methyl-1-benzamido-5-phenylcyclopent-2-ene-1,2-dicarboxylate

Base Information

• Chemical Name: (1S,5R)-2-ethyl 1-methyl-1-benzamido-5-phenylcyclopent-2-ene-1,2-dicarboxylate
• CAS No.: 1361559-76-3
• Molecular Formula: C₂₃H₂₃NO₅
• Molecular Weight: 393.439
• Mol file: 1361559-76-3.mol

Synonyms:(1S,5R)-2-ethyl 1-methyl-1-benzamido-5-phenylcyclopent-2-ene-1,2-dicarboxylate

Chemical Property of (1S,5R)-2-ethyl 1-methyl-1-benzamido-5-phenylcyclopent-2-ene-1,2-dicarboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,5R)-2-ethyl 1-methyl-1-benzamido-5-phenylcyclopent-2-ene-1,2-dicarboxylate

There total 2 articles about (1S,5R)-2-ethyl 1-methyl-1-benzamido-5-phenylcyclopent-2-ene-1,2-dicarboxylate 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: 58.0%

methanol (67-56-1) + ethyl 2,3-butadienoate (14369-81-4) + (4Z)-4-benzylidene-2-phenyl-1,3-oxazol-5(4H)-one (17606-70-1,5839-91-8) → rac-3-ethyl 1-methyl-1-benzamido-2-phenylcyclopent-3-ene-1,3-dicarboxylate (1361560-00-0) + (1S,5R)-2-ethyl 1-methyl-1-benzamido-5-phenylcyclopent-2-ene-1,2-dicarboxylate (1361559-76-3)

Guidance literature:

ethyl 2,3-butadienoate; (4Z)-4-benzylidene-2-phenyl-1,3-oxazol-5(4H)-one; With 4-t-butyl-4,5-dihydro-3H-dinaphtho[2,1-c;1',2'-e]phosphepine; In toluene; at 20 - 80 ℃; for 24h;

methanol; With chloro-trimethyl-silane; In toluene; at 0 - 20 ℃; optical yield given as %ee; enantioselective reaction;

DOI:10.1002/chem.201103502

Reference yield:

methanol (67-56-1) + ethyl 2,3-butadienoate (14369-81-4) + (4Z)-4-benzylidene-2-phenyl-1,3-oxazol-5(4H)-one (17606-70-1,5839-91-8) → C22H19NO4 (1361559-72-9) + (1R,5S)-2-ethyl 1-methyl-1-benzamido-5-phenylcyclopent-2-ene-1,2-dicarboxylate + (1S,5R)-2-ethyl 1-methyl-1-benzamido-5-phenylcyclopent-2-ene-1,2-dicarboxylate (1361559-76-3)

Guidance literature:

ethyl 2,3-butadienoate; (4Z)-4-benzylidene-2-phenyl-1,3-oxazol-5(4H)-one; With (R)-2,2'-bis(diphenylphosphanyl)-1,1'-binaphthyl; In toluene; at 20 ℃; Inert atmosphere;

methanol; With chloro-trimethyl-silane; In toluene; at 0 - 20 ℃; optical yield given as %ee; enantioselective reaction; Inert atmosphere;

DOI:10.1002/chem.201103502

Reference yield: 76.0%

(1S,5R)-2-ethyl 1-methyl-1-benzamido-5-phenylcyclopent-2-ene-1,2-dicarboxylate (1361559-76-3) → (1S,5R)-1-amino-5-phenylcyclopent-2-ene-1,2-dicarboxylic acid hydrochloride

Guidance literature:

With hydrogenchloride; In water; at 100 ℃; for 17h;

DOI:10.1002/chem.201103502

upstream raw materials:

methanol

ethyl 2,3-butadienoate

(4Z)-4-benzylidene-2-phenyl-1,3-oxazol-5(4H)-one

Downstream raw materials:

(1S,5R)-2-ethyl 1-methyl-1-benzamido-2-hydroxy-3-oxo-5-phenylcyclopentane-1,2-dicarboxylate