(2S,4R)-4-(tert-butyldimethylsilanyloxy)-2-[4-(p-nitrobenzyloxycarbonylaminomethylthiazol-2-yl)]-1-(p-nitrobenzyloxycarbonyl)pyrrolidine

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Chemical Name:(2S,4R)-4-(tert-butyldimethylsilanyloxy)-2-[4-(p-nitrobenzyloxycarbonylaminomethylthiazol-2-yl)]-1-(p-nitrobenzyloxycarbonyl)pyrrolidine
CAS No.:496048-70-5
Molecular Formula:C₃₀H₃₇N₅O₉SSi
Molecular Weight:671.803
Hs Code.:

(2S,4R)-4-(tert-butyldimethylsilanyloxy)-2-[4-(p-nitrobenzyloxycarbonylaminomethylthiazol-2-yl)]-1-(p-nitrobenzyloxycarbonyl)pyrrolidine

Synonyms:(2S,4R)-4-(tert-butyldimethylsilanyloxy)-2-[4-(p-nitrobenzyloxycarbonylaminomethylthiazol-2-yl)]-1-(p-nitrobenzyloxycarbonyl)pyrrolidine

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Chemical Property of (2S,4R)-4-(tert-butyldimethylsilanyloxy)-2-[4-(p-nitrobenzyloxycarbonylaminomethylthiazol-2-yl)]-1-(p-nitrobenzyloxycarbonyl)pyrrolidine

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Technology Process of (2S,4R)-4-(tert-butyldimethylsilanyloxy)-2-[4-(p-nitrobenzyloxycarbonylaminomethylthiazol-2-yl)]-1-(p-nitrobenzyloxycarbonyl)pyrrolidine

There total 9 articles about (2S,4R)-4-(tert-butyldimethylsilanyloxy)-2-[4-(p-nitrobenzyloxycarbonylaminomethylthiazol-2-yl)]-1-(p-nitrobenzyloxycarbonyl)pyrrolidine 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: 94.2%

: 4457-32-3
4-nitrobenzyl chloroformate

: 496048-68-1
(2S,4R)-2-(4-aminomethylthiazol-2-yl)-4-(tert-butyldimethylsilanyloxy)-1-(p-nitrobenzyloxycarbonyl)pyrrolidine

: 496048-70-5
(2S,4R)-4-(tert-butyldimethylsilanyloxy)-2-[4-(p-nitrobenzyloxycarbonylaminomethylthiazol-2-yl)]-1-(p-nitrobenzyloxycarbonyl)pyrrolidine

Guidance literature:: With triethylamine; In dichloromethane; at 0 ℃; for 1h;
DOI:10.1016/S0223-5234(02)01397-1

Reference yield:

: 2-[(2S,4R)-4-Hydroxy-1-(4-nitro-benzyloxycarbonyl)-pyrrolidin-2-yl]-thiazole-4-carboxylic acid ethyl ester

: 496048-70-5
(2S,4R)-4-(tert-butyldimethylsilanyloxy)-2-[4-(p-nitrobenzyloxycarbonylaminomethylthiazol-2-yl)]-1-(p-nitrobenzyloxycarbonyl)pyrrolidine

Guidance literature:: Multi-step reaction with 6 steps

1: 3.93 g / imidazole / dimethylformamide / 1.5 h / 20 °C

2: NaBH₄ / ethanol / 6 h / 0 °C

3: 4.11 g / Et₃N / CH₂Cl₂ / 1 h / 0 °C

4: dimethylformamide / 1 h / 100 °C

5: 1.36 g / hydrazine hydrate / CH₂Cl₂; methanol / 5 h / 60 °C

6: 94.2 percent / Et₃N / CH₂Cl₂ / 1 h / 0 °C

With 1H-imidazole; sodium tetrahydroborate; hydrazine hydrate; triethylamine; In methanol; ethanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/S0223-5234(02)01397-1

Reference yield:

: (2S,4R)-4-Benzoyloxy-2-carbamoyl-pyrrolidine-1-carboxylic acid 4-nitro-benzyl ester

: 496048-70-5
(2S,4R)-4-(tert-butyldimethylsilanyloxy)-2-[4-(p-nitrobenzyloxycarbonylaminomethylthiazol-2-yl)]-1-(p-nitrobenzyloxycarbonyl)pyrrolidine

Guidance literature:: Multi-step reaction with 9 steps

1: 94.7 percent / Lawesson's reagent / tetrahydrofuran / 2 h / Heating

2: 89.2 percent / ethanol / 20 h / 20 °C

3: KOH / methanol / 2 h / cooling

4: 3.93 g / imidazole / dimethylformamide / 1.5 h / 20 °C

5: NaBH₄ / ethanol / 6 h / 0 °C

6: 4.11 g / Et₃N / CH₂Cl₂ / 1 h / 0 °C

7: dimethylformamide / 1 h / 100 °C

8: 1.36 g / hydrazine hydrate / CH₂Cl₂; methanol / 5 h / 60 °C

9: 94.2 percent / Et₃N / CH₂Cl₂ / 1 h / 0 °C

With Lawessons reagent; 1H-imidazole; potassium hydroxide; sodium tetrahydroborate; hydrazine hydrate; triethylamine; In tetrahydrofuran; methanol; ethanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/S0223-5234(02)01397-1