1-Pyrrolidinecarboxylic acid, 2-[4-(cyanomethyl)-2-thiazolyl]-4-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-, (4-nitrophenyl)methyl ester, (2S,4R)-

Base Information

Chemical Name:1-Pyrrolidinecarboxylic acid, 2-[4-(cyanomethyl)-2-thiazolyl]-4-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-, (4-nitrophenyl)methyl ester, (2S,4R)-
CAS No.:496048-72-7
Molecular Formula:C23H30N4O5SSi
Molecular Weight:502.667
Hs Code.:

1-Pyrrolidinecarboxylic acid,
2-[4-(cyanomethyl)-2-thiazolyl]-4-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-,
(4-nitrophenyl)methyl ester, (2S,4R)-

Synonyms:

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Chemical Property of 1-Pyrrolidinecarboxylic acid, 2-[4-(cyanomethyl)-2-thiazolyl]-4-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-, (4-nitrophenyl)methyl ester, (2S,4R)-

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Technology Process of 1-Pyrrolidinecarboxylic acid, 2-[4-(cyanomethyl)-2-thiazolyl]-4-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-, (4-nitrophenyl)methyl ester, (2S,4R)-

There total 5 articles about 1-Pyrrolidinecarboxylic acid, 2-[4-(cyanomethyl)-2-thiazolyl]-4-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-, (4-nitrophenyl)methyl ester, (2S,4R)- 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: 78.5%

: 143-33-9,25596-52-5
sodium cyanide

: 496048-66-9
(2S,4R)-4-(tert-butyldimethylsilanyloxy)-2-(4-ethoxycarbonylthiazol-2-yl)-1-(p-nitrobenzyloxycarbonyl)pyrrolidine

: 496048-72-7
(2S,4R)-4-(tert-butyldimethylsilanyloxy)-2-(4-cyanomethylthiazol-2-yl)-1-(p-nitrobenzyloxycarbonyl)pyrrolidine

Guidance literature:: In dimethyl sulfoxide; at 70 ℃; for 8h;
DOI:10.1016/S0223-5234(02)01397-1

Reference yield:

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

: 496048-72-7
(2S,4R)-4-(tert-butyldimethylsilanyloxy)-2-(4-cyanomethylthiazol-2-yl)-1-(p-nitrobenzyloxycarbonyl)pyrrolidine

Guidance literature:: Multi-step reaction with 5 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: 78.5 percent / dimethylsulfoxide / 8 h / 70 °C

With Lawessons reagent; 1H-imidazole; potassium hydroxide; In tetrahydrofuran; methanol; ethanol; dimethyl sulfoxide; N,N-dimethyl-formamide;
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

: 496048-72-7
(2S,4R)-4-(tert-butyldimethylsilanyloxy)-2-(4-cyanomethylthiazol-2-yl)-1-(p-nitrobenzyloxycarbonyl)pyrrolidine

Guidance literature:: Multi-step reaction with 2 steps

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

2: 78.5 percent / dimethylsulfoxide / 8 h / 70 °C

With 1H-imidazole; In dimethyl sulfoxide; N,N-dimethyl-formamide;
DOI:10.1016/S0223-5234(02)01397-1