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

Base Information

• Chemical Name: (S)-1-[7-[(tert-butyldiphenylsilyl)oxy]naphthalen-1-yl]-2-oxo-3-({2-[1-(triphenylmethyl)-1H-imidazol-4-yl]ethyl}amino)pyrrolidine
• CAS No.: 440107-57-3
• Molecular Formula: C₅₄H₅₂N₄O₂Si
• Molecular Weight: 817.118

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

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

Chemical Property:

Purity/Quality:

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

There total 9 articles about (S)-1-[7-[(tert-butyldiphenylsilyl)oxy]naphthalen-1-yl]-2-oxo-3-({2-[1-(triphenylmethyl)-1H-imidazol-4-yl]ethyl}amino)pyrrolidine 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: 52.0%

(S)-N-{1-[7-[(tert-butyldiphenylsilyl)oxy]naphthalen-1-yl]-2-oxopyrrolidin-3-yl}-2-[1-(triphenylmethyl)-1H-imidazol-4-yl]thioacetamide (440105-69-1) → (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)

Guidance literature:

With sodium tetrahydroborate; nickel dichloride; In tetrahydrofuran; methanol;

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-oxo-3-({2-[1-(triphenylmethyl)-1H-imidazol-4-yl]ethyl}amino)pyrrolidine (440107-57-3)

Guidance literature:

Multi-step reaction with 11 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

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-oxo-3-({2-[1-(triphenylmethyl)-1H-imidazol-4-yl]ethyl}amino)pyrrolidine (440107-57-3)

Guidance literature:

Multi-step reaction with 10 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

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:

(S)-N-{1-[7-[(tert-butyldiphenylsilyl)oxy]naphthalen-1-yl]-2-oxopyrrolidin-3-yl}-2-[1-(triphenylmethyl)-1H-imidazol-4-yl]thioacetamide

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

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

(S)-3-[(tert-butoxycarbonyl)amino]-1-[7-[(tert-butyldimethylsilyl)oxy]naphthalen-1-yl]-2-oxopyrrolidine

Downstream raw materials:

(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

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

(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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