2-(4-benzoylamino-2-oxo-2H-pyrimidin-1-yl)-5-(tert-butyl-dimethyl-silanyloxymethyl)-3-trifluoromethyl-pyrrolidine-1-carboxylic acid tert-butyl ester

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Chemical Name:2-(4-benzoylamino-2-oxo-2H-pyrimidin-1-yl)-5-(tert-butyl-dimethyl-silanyloxymethyl)-3-trifluoromethyl-pyrrolidine-1-carboxylic acid tert-butyl ester
CAS No.:496848-44-3
Molecular Formula:C₂₈H₃₉F₃N₄O₅Si
Molecular Weight:596.722
Hs Code.:

2-(4-benzoylamino-2-oxo-2<i>H</i>-pyrimidin-1-yl)-5-(<i>tert</i>-butyl-dimethyl-silanyloxymethyl)-3-trifluoromethyl-pyrrolidine-1-carboxylic acid <i>tert</i>-butyl ester

Synonyms:2-(4-benzoylamino-2-oxo-2H-pyrimidin-1-yl)-5-(tert-butyl-dimethyl-silanyloxymethyl)-3-trifluoromethyl-pyrrolidine-1-carboxylic acid tert-butyl ester

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Chemical Property of 2-(4-benzoylamino-2-oxo-2H-pyrimidin-1-yl)-5-(tert-butyl-dimethyl-silanyloxymethyl)-3-trifluoromethyl-pyrrolidine-1-carboxylic acid tert-butyl ester

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Technology Process of 2-(4-benzoylamino-2-oxo-2H-pyrimidin-1-yl)-5-(tert-butyl-dimethyl-silanyloxymethyl)-3-trifluoromethyl-pyrrolidine-1-carboxylic acid tert-butyl ester

There total 9 articles about 2-(4-benzoylamino-2-oxo-2H-pyrimidin-1-yl)-5-(tert-butyl-dimethyl-silanyloxymethyl)-3-trifluoromethyl-pyrrolidine-1-carboxylic acid tert-butyl 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: 91.0%

: 93-97-0
benzoic acid anhydride

: 496848-38-5
tert-butyl (2RS,3S,5R)-2-[4-amino-2-oxopyrimidin-1(2H)-yl]-5-[(tert-butyldimethylsilyloxy)methyl]-3-(trifluoromethyl)pyrrolidine-1-carboxylate

: 496848-44-3
2-(4-benzoylamino-2-oxo-2H-pyrimidin-1-yl)-5-(tert-butyl-dimethyl-silanyloxymethyl)-3-trifluoromethyl-pyrrolidine-1-carboxylic acid tert-butyl ester

Guidance literature:: In dichloromethane; at 20 ℃; for 30h;
DOI:10.1135/cccc20021267

Reference yield:

: 102308-32-7
(4S)-4-formyl-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

: 496848-44-3
2-(4-benzoylamino-2-oxo-2H-pyrimidin-1-yl)-5-(tert-butyl-dimethyl-silanyloxymethyl)-3-trifluoromethyl-pyrrolidine-1-carboxylic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 9 steps

1.1: 93 percent / CH₂Cl₂ / 24 h / Heating

2.1: 62 percent / CuI / dimethylformamide; hexamethylphosphoric acid triamide / 30 h / 75 °C

3.1: 95 percent / H₂ / 10 percent Pd/C / ethyl acetate / 5 h / 20 °C / 760 Torr

4.1: 58 percent / aq. citric acid / methanol / 4 h / 60 °C

5.1: 92 percent / imidazole / CH₂Cl₂ / 2 h / 20 °C

6.1: 64 percent / DIBAL-H / CH₂Cl₂; cyclohexane / 3 h / -78 °C

7.1: 93 percent / DMAP / CH₂Cl₂ / 20 °C

8.1: N,O-bis(trimethylsilyl)acetamide / acetonitrile / 0.5 h / Heating

8.2: 95 percent / trimethylsilyl triflate / acetonitrile / 16 h / 20 °C

9.1: 91 percent / CH₂Cl₂ / 30 h / 20 °C

With 1H-imidazole; dmap; copper(l) iodide; N,O-bis-(trimethylsilyl)-acetamide; hydrogen; diisobutylaluminium hydride; citric acid; palladium on activated charcoal; In methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; dichloromethane; cyclohexane; ethyl acetate; N,N-dimethyl-formamide; acetonitrile; 1.1: Wittig reaction;
DOI:10.1135/cccc20021267

Reference yield:

: ethyl (Z)/(E)-3-[(S)-3-(tert-butoxycarbonyl)-2,2-dimethyloxazolidin-4-yl]-2-(trifluoromethyl)acrylate

: 496848-44-3
2-(4-benzoylamino-2-oxo-2H-pyrimidin-1-yl)-5-(tert-butyl-dimethyl-silanyloxymethyl)-3-trifluoromethyl-pyrrolidine-1-carboxylic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 7 steps

1.1: 95 percent / H₂ / 10 percent Pd/C / ethyl acetate / 5 h / 20 °C / 760 Torr

2.1: 58 percent / aq. citric acid / methanol / 4 h / 60 °C

3.1: 92 percent / imidazole / CH₂Cl₂ / 2 h / 20 °C

4.1: 64 percent / DIBAL-H / CH₂Cl₂; cyclohexane / 3 h / -78 °C

5.1: 93 percent / DMAP / CH₂Cl₂ / 20 °C

6.1: N,O-bis(trimethylsilyl)acetamide / acetonitrile / 0.5 h / Heating

6.2: 95 percent / trimethylsilyl triflate / acetonitrile / 16 h / 20 °C

7.1: 91 percent / CH₂Cl₂ / 30 h / 20 °C

With 1H-imidazole; dmap; N,O-bis-(trimethylsilyl)-acetamide; hydrogen; diisobutylaluminium hydride; citric acid; palladium on activated charcoal; In methanol; dichloromethane; cyclohexane; ethyl acetate; acetonitrile;
DOI:10.1135/cccc20021267