2-Propenoic acid, 2-[[(1,1-dimethylethoxy)carbonyl]amino]-3-phenyl-, methyl ester, (Z)-

Base Information

• Chemical Name: 2-Propenoic acid, 2-[[(1,1-dimethylethoxy)carbonyl]amino]-3-phenyl-, methyl ester, (Z)-
• CAS No.: 63658-18-4
• Molecular Formula: C15H19NO4
• Molecular Weight: 277.32
• Mol file: 63658-18-4.mol

Synonyms:(Z)-methyl 2-(tert-butoxycarbonylamino)-3-phenylacrylate;N-Boc-(Z)-aminocinnamic acid methyl ester;(Z)-methyl 2-((tert-butoxycarbonyl)amino)-3-phenylacrylate;(Z)-2-tert-Butoxycarbonylamino-3-phenyl-acrylic acid methyl ester;methyl (Z)-N-Boc-α,β-didehydrophenylalaninate;(Z)-methyl 2-((tert-butoxycarbonyl)amino)-3-phenyl-acrylate;Boc-Z-ΔPhe-OMe;

Chemical Property of 2-Propenoic acid, 2-[[(1,1-dimethylethoxy)carbonyl]amino]-3-phenyl-, methyl ester, (Z)-

Chemical Property:

• PSA: 64.63000
• LogP: 3.11610

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 2-Propenoic acid, 2-[[(1,1-dimethylethoxy)carbonyl]amino]-3-phenyl-, methyl ester, (Z)-

There total 32 articles about 2-Propenoic acid, 2-[[(1,1-dimethylethoxy)carbonyl]amino]-3-phenyl-, methyl ester, (Z)- 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: 93.0%

trimethyl 2-(tert-butoxycarbonylamino)phosphonoacetate (121056-95-9,89524-98-1) + benzaldehyde (100-52-7) → methyl (Z)-N-Boc-α,β-didehydrophenylalaninate (63658-18-4) + methyl (E)-N-Boc-α,β-didehydrophenylalaninate (63658-17-3)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; at 20 ℃;

DOI:10.1021/ol500219e

Reference yield: 92.0%

4-methyl 3-(1,1-dimethylethyl) cis-2-oxo-5-phenyl-3,4-oxazolidinedicarboxylate → methyl (Z)-N-Boc-α,β-didehydrophenylalaninate (63658-18-4) + methyl (E)-N-Boc-α,β-didehydrophenylalaninate (63658-17-3)

Guidance literature:

With lithium hexamethyldisilazane; In tetrahydrofuran; at -20 ℃; for 0.0833333h; stereoselective reaction; Inert atmosphere;

DOI:10.1246/bcsj.82.364

Reference yield: 92.0%

2-Isocyanato-3-phenylpropensaeure-methylester (103999-81-1) + tert-butyl alcohol (75-65-0) → methyl 2-(tert-butoxycarbonylamino)-3-phenylacrylate (63658-17-3,63658-18-4,63096-26-4)

Guidance literature:

at 80 ℃; for 14h;

upstream raw materials:

methyl 2-tert-butoxycarbonylamino-3-phenylpropanoate

methyl (2S,3R)-2-((tert-butoxycarbonyl)amino)-3-((methanesulfonyl)oxy)-3-phenylpropionate

2-Isocyanato-3-phenylpropensaeure-methylester

tert-butyl alcohol

Downstream raw materials:

Boc-α,β-Dehydrophenylalanin

methyl (2R)-2-(t-butoxycarbonylamino)-3-phenylpropionate

2-Isocyanato-3-phenylpropensaeure-methylester

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