(2S,4R)-4-Hydroxy-2-{4-[(4-nitro-benzyloxycarbonylamino)-methyl]-thiazol-2-yl}-pyrrolidine-1-carboxylic acid 4-nitro-benzyl ester

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Chemical Name:(2S,4R)-4-Hydroxy-2-{4-[(4-nitro-benzyloxycarbonylamino)-methyl]-thiazol-2-yl}-pyrrolidine-1-carboxylic acid 4-nitro-benzyl ester
CAS No.:496048-97-6
Molecular Formula:C₂₄H₂₃N₅O₉S
Molecular Weight:557.541
Hs Code.:

Synonyms:(2S,4R)-4-Hydroxy-2-{4-[(4-nitro-benzyloxycarbonylamino)-methyl]-thiazol-2-yl}-pyrrolidine-1-carboxylic acid 4-nitro-benzyl ester

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Chemical Property of (2S,4R)-4-Hydroxy-2-{4-[(4-nitro-benzyloxycarbonylamino)-methyl]-thiazol-2-yl}-pyrrolidine-1-carboxylic acid 4-nitro-benzyl ester

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Technology Process of (2S,4R)-4-Hydroxy-2-{4-[(4-nitro-benzyloxycarbonylamino)-methyl]-thiazol-2-yl}-pyrrolidine-1-carboxylic acid 4-nitro-benzyl ester

There total 10 articles about (2S,4R)-4-Hydroxy-2-{4-[(4-nitro-benzyloxycarbonylamino)-methyl]-thiazol-2-yl}-pyrrolidine-1-carboxylic acid 4-nitro-benzyl ester 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:

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

: 496048-97-6
(2S,4R)-4-Hydroxy-2-{4-[(4-nitro-benzyloxycarbonylamino)-methyl]-thiazol-2-yl}-pyrrolidine-1-carboxylic acid 4-nitro-benzyl ester

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 2h;
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

: 496048-97-6
(2S,4R)-4-Hydroxy-2-{4-[(4-nitro-benzyloxycarbonylamino)-methyl]-thiazol-2-yl}-pyrrolidine-1-carboxylic acid 4-nitro-benzyl ester

Guidance literature:: Multi-step reaction with 7 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

7: TBAF / tetrahydrofuran / 2 h / 20 °C

With 1H-imidazole; sodium tetrahydroborate; tetrabutyl ammonium fluoride; hydrazine hydrate; triethylamine; In tetrahydrofuran; 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

: 496048-97-6
(2S,4R)-4-Hydroxy-2-{4-[(4-nitro-benzyloxycarbonylamino)-methyl]-thiazol-2-yl}-pyrrolidine-1-carboxylic acid 4-nitro-benzyl ester

Guidance literature:: Multi-step reaction with 10 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

10: TBAF / tetrahydrofuran / 2 h / 20 °C

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