methyl (S,Z)-2-(2-((tert-butoxycarbonyl)amino)propanamido)-3-phenylacrylate

Base Information

Chemical Name:methyl (S,Z)-2-(2-((tert-butoxycarbonyl)amino)propanamido)-3-phenylacrylate
CAS No.:55478-15-4
Molecular Formula:C₁₈H₂₄N₂O₅
Molecular Weight:348.399
Hs Code.:

Synonyms:methyl (S,Z)-2-(2-((tert-butoxycarbonyl)amino)propanamido)-3-phenylacrylate

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Chemical Property of methyl (S,Z)-2-(2-((tert-butoxycarbonyl)amino)propanamido)-3-phenylacrylate

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Technology Process of methyl (S,Z)-2-(2-((tert-butoxycarbonyl)amino)propanamido)-3-phenylacrylate

There total 13 articles about methyl (S,Z)-2-(2-((tert-butoxycarbonyl)amino)propanamido)-3-phenylacrylate 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: 92.0%

: methyl 2-((S)-2-((tert-butoxycarbonyl)amino)propanamido)-3-hydroxy-3-phenylpropanoate

: 55478-15-4
methyl (S,Z)-2-(2-((tert-butoxycarbonyl)amino)propanamido)-3-phenylacrylate

Guidance literature:: methyl 2-((S)-2-((tert-butoxycarbonyl)amino)propanamido)-3-hydroxy-3-phenylpropanoate; With dmap; di-tert-butyl dicarbonate; In acetonitrile; at 20 ℃;

With N,N,N',N'-tetramethylguanidine; In acetonitrile;
DOI:10.1039/c5tb00501a

Reference yield:

: 69-96-5
Phenylserin

: 55478-15-4
methyl (S,Z)-2-(2-((tert-butoxycarbonyl)amino)propanamido)-3-phenylacrylate

Guidance literature:: Multi-step reaction with 3 steps

1.1: thionyl chloride / 16 h / 0 - 70 °C / Inert atmosphere

2.1: benzotriazol-1-ol; triethylamine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / water; dichloromethane / 22 h / 0 - 20 °C

3.1: dmap; di-tert-butyl dicarbonate / acetonitrile / 0 °C

3.2: 12 h

With dmap; thionyl chloride; di-tert-butyl dicarbonate; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In dichloromethane; water; acetonitrile;
DOI:10.1021/acs.orglett.6b03308

Reference yield:

: 80182-99-6
β-hydroxyphenylalanine methyl ester hydrochloride

: 55478-15-4
methyl (S,Z)-2-(2-((tert-butoxycarbonyl)amino)propanamido)-3-phenylacrylate

Guidance literature:: Multi-step reaction with 2 steps

1.1: benzotriazol-1-ol; triethylamine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / water; dichloromethane / 22 h / 0 - 20 °C

2.1: dmap; di-tert-butyl dicarbonate / acetonitrile / 0 °C

2.2: 12 h

With dmap; di-tert-butyl dicarbonate; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In dichloromethane; water; acetonitrile;
DOI:10.1021/acs.orglett.6b03308