3-{2-[(1S,2R,3S,4R)-3-((S)-2-Hydroxy-1-pentylcarbamoyl-ethylcarbamoyl)-7-oxa-bicyclo[2.2.1]hept-2-ylmethyl]-phenyl}-propionic acid methyl ester

Base Information

• Chemical Name: 3-{2-[(1S,2R,3S,4R)-3-((S)-2-Hydroxy-1-pentylcarbamoyl-ethylcarbamoyl)-7-oxa-bicyclo[2.2.1]hept-2-ylmethyl]-phenyl}-propionic acid methyl ester
• CAS No.: 147266-43-1
• Molecular Formula: C₂₆H₃₈N₂O₆
• Molecular Weight: 474.598
• Mol file: 147266-43-1.mol

Synonyms:3-{2-[(1S,2R,3S,4R)-3-((S)-2-Hydroxy-1-pentylcarbamoyl-ethylcarbamoyl)-7-oxa-bicyclo[2.2.1]hept-2-ylmethyl]-phenyl}-propionic acid methyl ester

Chemical Property of 3-{2-[(1S,2R,3S,4R)-3-((S)-2-Hydroxy-1-pentylcarbamoyl-ethylcarbamoyl)-7-oxa-bicyclo[2.2.1]hept-2-ylmethyl]-phenyl}-propionic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-{2-[(1S,2R,3S,4R)-3-((S)-2-Hydroxy-1-pentylcarbamoyl-ethylcarbamoyl)-7-oxa-bicyclo[2.2.1]hept-2-ylmethyl]-phenyl}-propionic acid methyl ester

There total 1 articles about 3-{2-[(1S,2R,3S,4R)-3-((S)-2-Hydroxy-1-pentylcarbamoyl-ethylcarbamoyl)-7-oxa-bicyclo[2.2.1]hept-2-ylmethyl]-phenyl}-propionic acid methyl ester 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:

(S)-2-Amino-3-hydroxy-N-pentyl-propionamide + <1S-(1α,2α,3α,4α)>-2-<(3-carboxy-7-oxabicyclo<2.2.1>hept-2-yl)methyl>benzenepropanoic acid methyl ester (142757-91-3) → 3-{2-[(1S,2R,3S,4R)-3-((S)-2-Hydroxy-1-pentylcarbamoyl-ethylcarbamoyl)-7-oxa-bicyclo[2.2.1]hept-2-ylmethyl]-phenyl}-propionic acid methyl ester (147266-43-1)

Guidance literature:

With 4-methyl-morpholine; isobutyl chloroformate; Yield given. Multistep reaction; 1.) DMF, -10 deg C, 2.) -10 to 25 deg C;

DOI:10.1016/S0040-4039(00)74756-3

Reference yield:

3-{2-[(1S,2R,3S,4R)-3-((S)-2-Hydroxy-1-pentylcarbamoyl-ethylcarbamoyl)-7-oxa-bicyclo[2.2.1]hept-2-ylmethyl]-phenyl}-propionic acid methyl ester (147266-43-1) → <1S-(1α,2α,3α,4α)>-2-<<3-<4-<(pentylamino)carbonyl>-2-oxazolyl>-7-oxabicyclo<2.2.1>hept-2-yl>methyl>benzenepropanoic acid methyl ester (142663-84-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) MsCl, Et₃N, 2.) K₂CO₃ / 1.) CH₂Cl₂, 0 deg C, 2.) acetone, 65 deg C

2: 10 percent / CuBr₂, hexamethylenetetramine, 1,8-diazabicyclo<5.4.0>undec-7-ene / CH₂Cl₂ / Ambient temperature

With hexamethylenetetramine; potassium carbonate; methanesulfonyl chloride; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; copper(ll) bromide; In dichloromethane;

DOI:10.1021/jo00068a059

Reference yield:

methanesulfonyl chloride (124-63-0) + 3-{2-[(1S,2R,3S,4R)-3-((S)-2-Hydroxy-1-pentylcarbamoyl-ethylcarbamoyl)-7-oxa-bicyclo[2.2.1]hept-2-ylmethyl]-phenyl}-propionic acid methyl ester (147266-43-1) → 3-{2-[(1S,2R,3S,4R)-3-((S)-2-Methanesulfonyloxy-1-pentylcarbamoyl-ethylcarbamoyl)-7-oxa-bicyclo[2.2.1]hept-2-ylmethyl]-phenyl}-propionic acid methyl ester

Guidance literature:

With triethylamine; In dichloromethane; at -10 ℃;

DOI:10.1016/S0040-4039(00)74756-3

upstream raw materials:

<1S-(1α,2α,3α,4α)>-2-<(3-carboxy-7-oxabicyclo<2.2.1>hept-2-yl)methyl>benzenepropanoic acid methyl ester

Downstream raw materials:

<1S-(1α,2α,3α,4α)>-2-<<3-<4-<(pentylamino)carbonyl>-2-oxazolyl>-7-oxabicyclo<2.2.1>hept-2-yl>methyl>benzenepropanoic acid methyl ester

[1S-(1α,2α,3β,4α)]-2-[[3-[4-[(Pentylamino)carbonyl]-2-oxazolyl]-7-oxabicyclo[2.2.1]hept-2-yl]methyl]benzenepropanoic acid

[1S-[1α,2α,3α(R*),4α]]-2-[[3-[[[1-Methylene-2-oxo-2-(pentylamino)ethyl]amino]carbonyl]-7-oxabicyclo[2.2.1]hept-2-yl]methyl]benzenepropanoic acid, methyl ester