(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

Base Information

• Chemical Name: (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
• CAS No.: 440105-70-4
• Molecular Formula: C₅₉H₆₀N₄O₄Si
• Molecular Weight: 917.235

Synonyms:(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

Chemical Property of (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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Useful:

Technology Process of (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

There total 9 articles about (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 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: 54.0%

di-tert-butyl dicarbonate (24424-99-5) + (S)-1-[7-[(tert-butyldiphenylsilyl)oxy]naphthalen-1-yl]-2-oxo-3-({2-[1-(triphenylmethyl)-1H-imidazol-4-yl]ethyl}amino)pyrrolidine (440107-57-3) → (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 (440105-70-4)

Guidance literature:

In N,N-dimethyl-formamide; at 20 ℃; for 18h;

DOI:10.1021/jm010531d

Reference yield:

t-butyl (7-hydroxynaphthalen-1-yl)carbamate (301548-32-3) → (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 (440105-70-4)

Guidance literature:

Multi-step reaction with 12 steps

1: 97 percent / imidazole / dimethylformamide / 0.5 h / 20 °C

2: 95 percent / HCl(gas) / ethyl acetate / 0.5 h / 20 °C

3: 85 percent / PyBOP; DIEA / CH₂Cl₂

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

5: 99 percent / TBAF / tetrahydrofuran / 0.25 h / 20 °C

6: 88 percent / imidazole / dimethylformamide / 3 h / 60 °C

7: 99 percent / TFA / CH₂Cl₂ / 0.5 h / 20 °C

8: 55 percent / HOBT; EDC; DIEA / dimethylformamide / 18 h / 20 °C

9: 43 percent / Lawesson's reagent / tetrahydrofuran / 15 h / 45 °C

10: 52 percent / NaBH₄; NiCl₂*6H₂O / methanol; tetrahydrofuran

11: 54 percent / dimethylformamide / 18 h / 20 °C

With Lawessons reagent; 1H-imidazole; hydrogenchloride; sodium tetrahydroborate; 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

Reference yield:

1-[(tert-butoxycarbonyl)amino]-7-[(tert-butyldimethylsilyl)oxy]naphthalene (440105-87-3) → (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 (440105-70-4)

Guidance literature:

Multi-step reaction with 11 steps

1: 95 percent / HCl(gas) / ethyl acetate / 0.5 h / 20 °C

2: 85 percent / PyBOP; DIEA / CH₂Cl₂

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

4: 99 percent / TBAF / tetrahydrofuran / 0.25 h / 20 °C

5: 88 percent / imidazole / dimethylformamide / 3 h / 60 °C

6: 99 percent / TFA / CH₂Cl₂ / 0.5 h / 20 °C

7: 55 percent / HOBT; EDC; DIEA / dimethylformamide / 18 h / 20 °C

8: 43 percent / Lawesson's reagent / tetrahydrofuran / 15 h / 45 °C

9: 52 percent / NaBH₄; NiCl₂*6H₂O / methanol; tetrahydrofuran

10: 54 percent / dimethylformamide / 18 h / 20 °C

With Lawessons reagent; 1H-imidazole; hydrogenchloride; sodium tetrahydroborate; 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

upstream raw materials:

di-tert-butyl dicarbonate

(S)-1-[7-[(tert-butyldiphenylsilyl)oxy]naphthalen-1-yl]-2-oxo-3-({2-[1-(triphenylmethyl)-1H-imidazol-4-yl]ethyl}amino)pyrrolidine

t-butyl (7-hydroxynaphthalen-1-yl)carbamate

1-[(tert-butoxycarbonyl)amino]-7-[(tert-butyldimethylsilyl)oxy]naphthalene

Downstream raw materials:

(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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