2-Butenoic acid, 4-[[(1,1-dimethylethoxy)carbonyl]methylamino]-3-phenyl-, methyl ester, (2Z)-

Base Information

• Chemical Name: 2-Butenoic acid, 4-[[(1,1-dimethylethoxy)carbonyl]methylamino]-3-phenyl-, methyl ester, (2Z)-
• CAS No.: 402938-21-0
• Molecular Formula: C17H23NO4
• Molecular Weight: 305.374
• Mol file: 402938-21-0.mol

Synonyms:

Chemical Property of 2-Butenoic acid, 4-[[(1,1-dimethylethoxy)carbonyl]methylamino]-3-phenyl-, methyl ester, (2Z)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-Butenoic acid, 4-[[(1,1-dimethylethoxy)carbonyl]methylamino]-3-phenyl-, methyl ester, (2Z)-

There total 7 articles about 2-Butenoic acid, 4-[[(1,1-dimethylethoxy)carbonyl]methylamino]-3-phenyl-, methyl ester, (2Z)- 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: 88.0%

tert-butyl 3-(2-methoxy-2-oxo-ethylidene)azetidine-1-carboxylate (1105662-87-0) + phenylboronic acid (98-80-6) → (Z)-methyl 3-[[(1,1-dimethylethoxycarbonyl)methylamino]methyl]-3-phenyl-2-propenoate (402938-21-0)

Guidance literature:

With tert-Amyl alcohol; chlorobis(cyclooctene)rhodium(I) dimer; 1,3-bis(bis(4-(trifluoromethyl)phenyl)phosphino)propane; sodium t-butanolate; at 110 ℃; for 8h; Reagent/catalyst; Schlenk technique; Inert atmosphere;

DOI:10.1039/c9cc06446j

Reference yield: 74.0%

tert-butyl N,N-dimethylcarbamate (7541-17-5) + (Z)-methyl 3-iodo-3-phenyl-propenoate (154026-89-8) → (Z)-methyl 3-[[(1,1-dimethylethoxycarbonyl)methylamino]methyl]-3-phenyl-2-propenoate (402938-21-0)

Guidance literature:

tert-butyl N,N-dimethylcarbamate; With sec.-butyllithium; (-)-sparteine; In tetrahydrofuran; cyclohexane; at -78 ℃; for 1h;

In tetrahydrofuran; at -78 - -55 ℃; for 1h;

(Z)-methyl 3-iodo-3-phenyl-propenoate; In tetrahydrofuran; at -55 - 20 ℃; Further stages.;

DOI:10.1021/jo016053w

Reference yield:

tert-butyl N,N-dimethylcarbamate (7541-17-5) + phenylpropynoic acid methyl ester (4891-38-7) → methyl 3-[[[(1,1-dimethylethoxy)carbonyl]methylamino]methyl]-3-phenyl-2-propenoate + (Z)-methyl 3-[[(1,1-dimethylethoxycarbonyl)methylamino]methyl]-3-phenyl-2-propenoate (402938-21-0)

Guidance literature:

tert-butyl N,N-dimethylcarbamate; With sec.-butyllithium; (-)-sparteine; In tetrahydrofuran; at -78 ℃; for 1.25h;

In tetrahydrofuran; at -78 - -55 ℃; for 0.75h;

phenylpropynoic acid methyl ester; With chloro-trimethyl-silane; In tetrahydrofuran; at -60 - 20 ℃; Further stages. Title compound not separated from byproducts.;

DOI:10.1021/jo0056038

upstream raw materials:

tert-butyl N,N-dimethylcarbamate

phenylpropynoic acid methyl ester

(Z)-methyl 3-iodo-3-phenyl-propenoate

phenylacetylene

Downstream raw materials:

1,5-dihydro-1-methyl-4-phenyl-2H-pyrrol-2-one

Refernces

• 1、 Dieter, R. Karl,Lu, Kai. "α-(N-carbamoyl)alkylcuprate chemistry in the synthesis of nitrogen heterocycles". . p. 847 - 855. Retrieved 2007/10/03.