(S)-methyl 2-(2-(4-(benzyloxy)phenyl)-1-(tert-butoxy-carbonylamino)ethyl)thiazole-4-carboxylate

Base Information

Chemical Name:(S)-methyl 2-(2-(4-(benzyloxy)phenyl)-1-(tert-butoxy-carbonylamino)ethyl)thiazole-4-carboxylate
CAS No.:932406-27-4
Molecular Formula:C₂₅H₂₈N₂O₅S
Molecular Weight:468.574
Hs Code.:

Synonyms:(S)-methyl 2-(2-(4-(benzyloxy)phenyl)-1-(tert-butoxy-carbonylamino)ethyl)thiazole-4-carboxylate

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Chemical Property of (S)-methyl 2-(2-(4-(benzyloxy)phenyl)-1-(tert-butoxy-carbonylamino)ethyl)thiazole-4-carboxylate

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Technology Process of (S)-methyl 2-(2-(4-(benzyloxy)phenyl)-1-(tert-butoxy-carbonylamino)ethyl)thiazole-4-carboxylate

There total 6 articles about (S)-methyl 2-(2-(4-(benzyloxy)phenyl)-1-(tert-butoxy-carbonylamino)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: 80.0%

: 932406-26-3
(S)-methyl 2-((S)-3-(4-(benzyloxy)phenyl)-2-(tert-butoxy-carbonylamino)propanethioamido)-3-hydroxypropanoate

: 932406-27-4
(S)-methyl 2-(2-(4-(benzyloxy)phenyl)-1-(tert-butoxy-carbonylamino)ethyl)thiazole-4-carboxylate

Guidance literature:: (S)-methyl 2-((S)-3-(4-(benzyloxy)phenyl)-2-(tert-butoxy-carbonylamino)propanethioamido)-3-hydroxypropanoate; With diethylamino-sulfur trifluoride; In dichloromethane; at -78 ℃; for 0.5h;

With Bromotrichloromethane; 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; at -40 - 20 ℃; Further stages.;
DOI:10.1016/j.tetlet.2007.01.034

Reference yield:

: 932406-25-2
(S)-methyl 2-((S)-2-(4-(benzyloxy)phenyl)-1-(tert-butoxy-carbonylamino)ethyl)-4,5-dihydrooxazole-4-carboxylate

: 932406-27-4
(S)-methyl 2-(2-(4-(benzyloxy)phenyl)-1-(tert-butoxy-carbonylamino)ethyl)thiazole-4-carboxylate

Guidance literature:: Multi-step reaction with 2 steps

1.1: 92 percent / H₂S; Et₃N / methanol / 20 °C

2.1: diethylaminosulfur trifluoride / CH₂Cl₂ / 0.5 h / -78 °C

2.2: 80 percent / DBU; BrCCl₃ / CH₂Cl₂ / -40 - 20 °C

With diethylamino-sulfur trifluoride; hydrogen sulfide; triethylamine; In methanol; dichloromethane;
DOI:10.1016/j.tetlet.2007.01.034

Reference yield:

: 24424-99-5
di-tert-butyl dicarbonate

: 932406-27-4
(S)-methyl 2-(2-(4-(benzyloxy)phenyl)-1-(tert-butoxy-carbonylamino)ethyl)thiazole-4-carboxylate

Guidance literature:: Multi-step reaction with 5 steps

1.1: 2.46 g / NaOH / H₂O; 2-methyl-propan-2-ol / 20 °C

2.1: 3.3 g / 1-hydroxybenzotriazole monohydrate; triethylamine; DCC / CH₂Cl₂ / 2 h / 0 - 20 °C

3.1: 87 percent / diethylaminosulfur trifluoride / CH₂Cl₂ / 1 h / -78 °C

4.1: 92 percent / H₂S; Et₃N / methanol / 20 °C

5.1: diethylaminosulfur trifluoride / CH₂Cl₂ / 0.5 h / -78 °C

5.2: 80 percent / DBU; BrCCl₃ / CH₂Cl₂ / -40 - 20 °C

With sodium hydroxide; diethylamino-sulfur trifluoride; hydrogen sulfide; 1-hydroxybenzotriazol-hydrate; triethylamine; dicyclohexyl-carbodiimide; In methanol; dichloromethane; water; tert-butyl alcohol;
DOI:10.1016/j.tetlet.2007.01.034