(S,Z)-methyl 2-[3-(octadec-9-en-1-yl)ureido]-3-phenylpropanoate

Base Information

• Chemical Name: (S,Z)-methyl 2-[3-(octadec-9-en-1-yl)ureido]-3-phenylpropanoate
• CAS No.: 1606178-86-2
• Molecular Formula: C₂₉H₄₈N₂O₃
• Molecular Weight: 472.712
• Mol file: 1606178-86-2.mol

Synonyms:

Chemical Property of (S,Z)-methyl 2-[3-(octadec-9-en-1-yl)ureido]-3-phenylpropanoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S,Z)-methyl 2-[3-(octadec-9-en-1-yl)ureido]-3-phenylpropanoate

There total 6 articles about (S,Z)-methyl 2-[3-(octadec-9-en-1-yl)ureido]-3-phenylpropanoate 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:

N-((Z)-octadec-9-en-1-yl)-1H-imidazole-1-carboxamide + methyl (2S)-2-amino-3-phenylpropanoate (2577-90-4) → (S,Z)-methyl 2-[3-(octadec-9-en-1-yl)ureido]-3-phenylpropanoate (1606178-86-2)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20 ℃;

DOI:10.1021/acs.jmedchem.8b00029

Reference yield:

(S)-2-tert-butoxycarbonylamino-3-phenyl-propionic acid methyl ester (51987-73-6) → (S,Z)-methyl 2-[3-(octadec-9-en-1-yl)ureido]-3-phenylpropanoate (1606178-86-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 2-chloropyridine; trifluoromethylsulfonic anhydride / dichloromethane / 0.83 h / 20 °C

2: dichloromethane / 20 h / 20 °C

With 2-chloropyridine; trifluoromethylsulfonic anhydride; In dichloromethane;

DOI:10.1021/jo500492x

Reference yield:

(Z)-9-octadecenoyl chloride (112-77-6) → (S,Z)-methyl 2-[3-(octadec-9-en-1-yl)ureido]-3-phenylpropanoate (1606178-86-2)

Guidance literature:

Multi-step reaction with 4 steps

1: ammonium hydroxide / tetrahydrofuran / 0 - 20 °C

2: lithium aluminium tetrahydride / tetrahydrofuran / 0 °C / Reflux

3: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 0 - 20 °C

4: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 20 °C

With ammonium hydroxide; lithium aluminium tetrahydride; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; N,N-dimethyl-formamide;

DOI:10.1021/acs.jmedchem.8b00029

upstream raw materials:

(S)-2-tert-butoxycarbonylamino-3-phenyl-propionic acid methyl ester

(Z)-9-octadecen-1-amine

methyl (S)-2-isocyanato-3-phenylpropanoate

(Z)-9-octadecenoyl chloride

Refernces

• 1、 Spyropoulos, Constantinos,Kokotos, Christoforos G.. "One-pot synthesis of ureas from Boc-protected amines". . p. 4477 - 4483. Retrieved 2014/06/09.