tert-butyl 2-((R)-1-(((S)-3-amino-2-methyl-3-oxopropyl)diphenylsilyl)-2-phenylethylcarbamoyl)pyrrolidine-1-carboxylate

Base Information

• Chemical Name: tert-butyl 2-((R)-1-(((S)-3-amino-2-methyl-3-oxopropyl)diphenylsilyl)-2-phenylethylcarbamoyl)pyrrolidine-1-carboxylate
• CAS No.: 1394293-54-9
• Molecular Formula: C₃₄H₄₃N₃O₄Si
• Molecular Weight: 585.819

Synonyms:tert-butyl 2-((R)-1-(((S)-3-amino-2-methyl-3-oxopropyl)diphenylsilyl)-2-phenylethylcarbamoyl)pyrrolidine-1-carboxylate

Chemical Property of tert-butyl 2-((R)-1-(((S)-3-amino-2-methyl-3-oxopropyl)diphenylsilyl)-2-phenylethylcarbamoyl)pyrrolidine-1-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Technology Process of tert-butyl 2-((R)-1-(((S)-3-amino-2-methyl-3-oxopropyl)diphenylsilyl)-2-phenylethylcarbamoyl)pyrrolidine-1-carboxylate

There total 11 articles about tert-butyl 2-((R)-1-(((S)-3-amino-2-methyl-3-oxopropyl)diphenylsilyl)-2-phenylethylcarbamoyl)pyrrolidine-1-carboxylate 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: 65.0%

1-(tert-butoxycarbonyl)-L-proline (15761-39-4,59433-50-0) + (S)-3-(((R)-1-amino-2-phenylethyl)diphenylsilyl)-2-methylpropanamide (1394293-56-1) → tert-butyl 2-((R)-1-(((S)-3-amino-2-methyl-3-oxopropyl)diphenylsilyl)-2-phenylethylcarbamoyl)pyrrolidine-1-carboxylate (1394293-54-9)

Guidance literature:

With 4-methyl-morpholine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In dichloromethane; N,N-dimethyl-formamide; at -10 - 20 ℃; for 14h;

DOI:10.1021/ol301933n

Reference yield:

(S)-3-(((R)-1-(1,3-dioxoisoindolin-2-yl)-2-phenylethyl)diphenylsilyl)-2-methylpropanoic acid (1394293-52-7) → tert-butyl 2-((R)-1-(((S)-3-amino-2-methyl-3-oxopropyl)diphenylsilyl)-2-phenylethylcarbamoyl)pyrrolidine-1-carboxylate (1394293-54-9)

Guidance literature:

Multi-step reaction with 3 steps

1: triethylamine; chloroformic acid ethyl ester; ammonium hydroxide / tetrahydrofuran / 2 h / -20 - -5 °C

2: hydrazine / ethanol / 14 h / Reflux

3: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; 4-methyl-morpholine / dichloromethane; N,N-dimethyl-formamide / 14 h / -10 - 20 °C

With 4-methyl-morpholine; ammonium hydroxide; chloroformic acid ethyl ester; triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; hydrazine; In tetrahydrofuran; ethanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/ol301933n

Reference yield:

2-((R)-1-(((S)-2-methylbut-3-enyl)diphenylsilyl)-2-phenylethyl)isoindoline-1,3-dione (1394293-51-6) → tert-butyl 2-((R)-1-(((S)-3-amino-2-methyl-3-oxopropyl)diphenylsilyl)-2-phenylethylcarbamoyl)pyrrolidine-1-carboxylate (1394293-54-9)

Guidance literature:

Multi-step reaction with 5 steps

1.1: triphenylphosphine; ozone / methanol; dichloromethane / -78 - 20 °C / Inert atmosphere

2.1: sodium dihydrogenphosphate; 2-methyl-but-2-ene / tert-butyl alcohol; water / 0.5 h

2.2: 2 h

3.1: triethylamine; chloroformic acid ethyl ester; ammonium hydroxide / tetrahydrofuran / 2 h / -20 - -5 °C

4.1: hydrazine / ethanol / 14 h / Reflux

5.1: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; 4-methyl-morpholine / dichloromethane; N,N-dimethyl-formamide / 14 h / -10 - 20 °C

With 4-methyl-morpholine; ammonium hydroxide; sodium dihydrogenphosphate; 2-methyl-but-2-ene; chloroformic acid ethyl ester; ozone; triethylamine; triphenylphosphine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; hydrazine; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; N,N-dimethyl-formamide; tert-butyl alcohol;

DOI:10.1021/ol301933n

upstream raw materials:

2-((R)-1-(((S)-2-methylbut-3-enyl)diphenylsilyl)-2-phenylethyl)isoindoline-1,3-dione

(S)-3-(((R)-1-(1,3-dioxoisoindolin-2-yl)-2-phenylethyl)diphenylsilyl)-2-methylpropanoic acid

(S)-3-(((R)-1-(1,3-dioxoisoindolin-2-yl)-2-phenylethyl)diphenylsilyl)-2-methylpropanamide

1-(tert-butoxycarbonyl)-L-proline

Downstream raw materials:

N-((R)-1-(((S)-3-amino-2-methyl-3-oxopropyl)dihydroxysilyl)-2-phenylethyl)pyrrolidine-2-carboxamide

C₁₇H₂₅F₂N₃O₂Si

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