(S)-{1-[7-[(tert-butyldiphenylsilyl)oxy]naphthalen-1-yl]-2-oxopyrrolidin-3-yl}-{2-[3-(4-cyano-3-fluorobenzyl)-3H-imidazol-4-yl]ethyl}carbamic acid tert-butyl ester

Base Information

Chemical Name:(S)-{1-[7-[(tert-butyldiphenylsilyl)oxy]naphthalen-1-yl]-2-oxopyrrolidin-3-yl}-{2-[3-(4-cyano-3-fluorobenzyl)-3H-imidazol-4-yl]ethyl}carbamic acid tert-butyl ester
CAS No.:440105-71-5
Molecular Formula:C₄₈H₅₀FN₅O₄Si
Molecular Weight:808.04
Hs Code.:

(S)-{1-[7-[(tert-butyldiphenylsilyl)oxy]naphthalen-1-yl]-2-oxopyrrolidin-3-yl}-{2-[3-(4-cyano-3-fluorobenzyl)-3H-imidazol-4-yl]ethyl}carbamic acid tert-butyl ester

Synonyms:(S)-{1-[7-[(tert-butyldiphenylsilyl)oxy]naphthalen-1-yl]-2-oxopyrrolidin-3-yl}-{2-[3-(4-cyano-3-fluorobenzyl)-3H-imidazol-4-yl]ethyl}carbamic acid tert-butyl ester

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Chemical Property of (S)-{1-[7-[(tert-butyldiphenylsilyl)oxy]naphthalen-1-yl]-2-oxopyrrolidin-3-yl}-{2-[3-(4-cyano-3-fluorobenzyl)-3H-imidazol-4-yl]ethyl}carbamic acid tert-butyl ester

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Purity/Quality:: 98% ^*data from raw suppliers

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Technology Process of (S)-{1-[7-[(tert-butyldiphenylsilyl)oxy]naphthalen-1-yl]-2-oxopyrrolidin-3-yl}-{2-[3-(4-cyano-3-fluorobenzyl)-3H-imidazol-4-yl]ethyl}carbamic acid tert-butyl ester

There total 14 articles about (S)-{1-[7-[(tert-butyldiphenylsilyl)oxy]naphthalen-1-yl]-2-oxopyrrolidin-3-yl}-{2-[3-(4-cyano-3-fluorobenzyl)-3H-imidazol-4-yl]ethyl}carbamic 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: 82.0%

: 222978-02-1
2-fluoro-4-(hydroxymethyl)benzonitrile

: 440105-70-4
(S)-{1-[7-[(tert-butyldiphenylsilyl)oxy]naphthalen-1-yl]-2-oxopyrrolidin-3-yl}-{2-[1-(triphenylmethyl)-1H-imidazol-4-yl]ethyl}carbamic acid tert-butyl ester

: 440105-71-5
(S)-{1-[7-[(tert-butyldiphenylsilyl)oxy]naphthalen-1-yl]-2-oxopyrrolidin-3-yl}-{2-[3-(4-cyano-3-fluorobenzyl)-3H-imidazol-4-yl]ethyl}carbamic acid tert-butyl ester

Guidance literature:: 2-fluoro-4-(hydroxymethyl)benzonitrile; (S)-{1-[7-[(tert-butyldiphenylsilyl)oxy]naphthalen-1-yl]-2-oxopyrrolidin-3-yl}-{2-[1-(triphenylmethyl)-1H-imidazol-4-yl]ethyl}carbamic acid tert-butyl ester; With trifluoromethylsulfonic anhydride; N-ethyl-N,N-diisopropylamine; In dichloromethane; at -78 - 0 ℃; for 18h;

In methanol; for 3h; Further stages.; Heating;
DOI:10.1021/jm010531d

Reference yield:

: 85070-67-3
2-fluoro-4-methylbenzonitrile

: 440105-71-5
(S)-{1-[7-[(tert-butyldiphenylsilyl)oxy]naphthalen-1-yl]-2-oxopyrrolidin-3-yl}-{2-[3-(4-cyano-3-fluorobenzyl)-3H-imidazol-4-yl]ethyl}carbamic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 4 steps

1.1: 65 percent / NBS; AIBN / CCl₄ / 24 h / Heating

2.1: 77 percent / aq. AgNO₃ / ethanol / 3 h / Heating

3.1: 98 percent / NaBH₄ / ethanol / 0.17 h / 0 °C

4.1: Tf₂O; DIEA / CH₂Cl₂ / 18 h / -78 - 0 °C

4.2: 82 percent / methanol / 3 h / Heating

With sodium tetrahydroborate; N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile); trifluoromethylsulfonic anhydride; silver nitrate; N-ethyl-N,N-diisopropylamine; In tetrachloromethane; ethanol; dichloromethane;
DOI:10.1021/jm010531d

Reference yield:

: 301548-32-3
t-butyl (7-hydroxynaphthalen-1-yl)carbamate

: 440105-71-5
(S)-{1-[7-[(tert-butyldiphenylsilyl)oxy]naphthalen-1-yl]-2-oxopyrrolidin-3-yl}-{2-[3-(4-cyano-3-fluorobenzyl)-3H-imidazol-4-yl]ethyl}carbamic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 13 steps

1.1: 97 percent / imidazole / dimethylformamide / 0.5 h / 20 °C

2.1: 95 percent / HCl(gas) / ethyl acetate / 0.5 h / 20 °C

3.1: 85 percent / PyBOP; DIEA / CH₂Cl₂

4.1: LiN(SiMe₃)2 / tetrahydrofuran / 0 °C

5.1: 99 percent / TBAF / tetrahydrofuran / 0.25 h / 20 °C

6.1: 88 percent / imidazole / dimethylformamide / 3 h / 60 °C

7.1: 99 percent / TFA / CH₂Cl₂ / 0.5 h / 20 °C

8.1: 55 percent / HOBT; EDC; DIEA / dimethylformamide / 18 h / 20 °C

9.1: 43 percent / Lawesson's reagent / tetrahydrofuran / 15 h / 45 °C

10.1: 52 percent / NaBH₄; NiCl₂*6H₂O / methanol; tetrahydrofuran

11.1: 54 percent / dimethylformamide / 18 h / 20 °C

12.1: Tf₂O; DIEA / CH₂Cl₂ / 18 h / -78 - 0 °C

12.2: 82 percent / methanol / 3 h / Heating

With Lawessons reagent; 1H-imidazole; hydrogenchloride; sodium tetrahydroborate; trifluoromethylsulfonic anhydride; tetrabutyl ammonium fluoride; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; nickel dichloride; lithium hexamethyldisilazane; In tetrahydrofuran; methanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide;
DOI:10.1021/jm010531d