ethyl (S)-2-(1-((tert-butoxycarbonyl)amino)-2-(4-((tert-butyldimethylsilyl)oxy)phenyl)ethyl)thiazole-4-carboxylate

Base Information

Chemical Name:ethyl (S)-2-(1-((tert-butoxycarbonyl)amino)-2-(4-((tert-butyldimethylsilyl)oxy)phenyl)ethyl)thiazole-4-carboxylate
CAS No.:1056753-77-5
Molecular Formula:C₂₅H₃₈N₂O₅SSi
Molecular Weight:506.739
Hs Code.:

Synonyms:ethyl (S)-2-(1-((tert-butoxycarbonyl)amino)-2-(4-((tert-butyldimethylsilyl)oxy)phenyl)ethyl)thiazole-4-carboxylate

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Chemical Property of ethyl (S)-2-(1-((tert-butoxycarbonyl)amino)-2-(4-((tert-butyldimethylsilyl)oxy)phenyl)ethyl)thiazole-4-carboxylate

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Technology Process of ethyl (S)-2-(1-((tert-butoxycarbonyl)amino)-2-(4-((tert-butyldimethylsilyl)oxy)phenyl)ethyl)thiazole-4-carboxylate

There total 5 articles about ethyl (S)-2-(1-((tert-butoxycarbonyl)amino)-2-(4-((tert-butyldimethylsilyl)oxy)phenyl)ethyl)thiazole-4-carboxylate 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: 90.0%

: 70-23-5
ethyl Bromopyruvate

: 1056753-74-2
tert-butyl (S)-(1-amino-3-(4-((tert-butyldimethylsilyl)oxy)phenyl)-1-thioxopropan-2-yl)carbamate

: 1056753-77-5
ethyl (S)-2-(1-((tert-butoxycarbonyl)amino)-2-(4-((tert-butyldimethylsilyl)oxy)phenyl)ethyl)thiazole-4-carboxylate

Guidance literature:: tert-butyl (S)-(1-amino-3-(4-((tert-butyldimethylsilyl)oxy)phenyl)-1-thioxopropan-2-yl)carbamate; With potassium hydrogencarbonate; In 1,2-dimethoxyethane; for 0.25h;

ethyl Bromopyruvate; In 1,2-dimethoxyethane; for 3h;

With 2,6-dimethylpyridine; trifluoroacetic anhydride; In 1,2-dimethoxyethane; at 0 ℃;

Reference yield:

: 3978-80-1
Boc-Tyr-OH

: 1056753-77-5
ethyl (S)-2-(1-((tert-butoxycarbonyl)amino)-2-(4-((tert-butyldimethylsilyl)oxy)phenyl)ethyl)thiazole-4-carboxylate

Guidance literature:: Multi-step reaction with 4 steps

1.1: 1H-imidazole / dichloromethane / 0.33 h / 20 °C

1.2: 20 °C

2.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine / N,N-dimethyl-formamide / 0.33 h / 20 °C

2.2: 20 °C

3.1: Lawessons reagent / 1,2-dimethoxyethane / 6 h / 20 °C

4.1: potassium hydrogencarbonate / 1,2-dimethoxyethane / 0.25 h / 20 °C

4.2: 3 h / 20 °C

4.3: 5 h / 5 - 20 °C

With Lawessons reagent; 1H-imidazole; benzotriazol-1-ol; potassium hydrogencarbonate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In 1,2-dimethoxyethane; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/acs.jmedchem.1c01583

Reference yield:

: 94732-15-7
(S)-2-(2-N-tert-butoxycarbonylamino)-3-[4-(tert-butyldimethylsilyloxy)phenyl]-propanoic acid

: 1056753-77-5
ethyl (S)-2-(1-((tert-butoxycarbonyl)amino)-2-(4-((tert-butyldimethylsilyl)oxy)phenyl)ethyl)thiazole-4-carboxylate

Guidance literature:: Multi-step reaction with 3 steps

1.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine / N,N-dimethyl-formamide / 0.33 h / 20 °C

1.2: 20 °C

2.1: Lawessons reagent / 1,2-dimethoxyethane / 6 h / 20 °C

3.1: potassium hydrogencarbonate / 1,2-dimethoxyethane / 0.25 h / 20 °C

3.2: 3 h / 20 °C

3.3: 5 h / 5 - 20 °C

With Lawessons reagent; benzotriazol-1-ol; potassium hydrogencarbonate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In 1,2-dimethoxyethane; N,N-dimethyl-formamide;
DOI:10.1021/acs.jmedchem.1c01583