(S)-ethyl 1-((S)-2-((tert-butoxycarbonyl)amino)-3-phenylpropanoyl)pyrrolidine-2-carboxylate

Base Information

• Chemical Name: (S)-ethyl 1-((S)-2-((tert-butoxycarbonyl)amino)-3-phenylpropanoyl)pyrrolidine-2-carboxylate
• CAS No.: 1427166-47-9
• Molecular Formula: C₂₁H₃₀N₂O₅
• Molecular Weight: 390.48

Synonyms:(S)-ethyl 1-((S)-2-((tert-butoxycarbonyl)amino)-3-phenylpropanoyl)pyrrolidine-2-carboxylate

Chemical Property of (S)-ethyl 1-((S)-2-((tert-butoxycarbonyl)amino)-3-phenylpropanoyl)pyrrolidine-2-carboxylate

Chemical Property:

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Technology Process of (S)-ethyl 1-((S)-2-((tert-butoxycarbonyl)amino)-3-phenylpropanoyl)pyrrolidine-2-carboxylate

There total 2 articles about (S)-ethyl 1-((S)-2-((tert-butoxycarbonyl)amino)-3-phenylpropanoyl)pyrrolidine-2-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: 90.0%

ethyl (2S)-pyrrolidine-2-carboxylate (5817-26-5) + (S)-tert-butyl (1-(1H-benzo[d][1,2,3]triazol-1-yl)-1-oxo-3-phenylpropan-2-yl)carbamate (514214-66-5) → (S)-ethyl 1-((S)-2-((tert-butoxycarbonyl)amino)-3-phenylpropanoyl)pyrrolidine-2-carboxylate (1427166-47-9)

Guidance literature:

With triethylamine; In water; acetonitrile; at -40 - 25 ℃; for 16h;

DOI:10.1039/c3cc39291k

Reference yield:

N-tert-butoxycarbonyl-L-phenylalanine (13734-34-4) → (S)-ethyl 1-((S)-2-((tert-butoxycarbonyl)amino)-3-phenylpropanoyl)pyrrolidine-2-carboxylate (1427166-47-9)

Guidance literature:

Multi-step reaction with 2 steps

1.1: dicyclohexyl-carbodiimide / dichloromethane / 0.5 h / Inert atmosphere

1.2: 12 h / 25 °C / Inert atmosphere

2.1: triethylamine / acetonitrile; water / 16 h / -40 - 25 °C

With triethylamine; dicyclohexyl-carbodiimide; In dichloromethane; water; acetonitrile;

DOI:10.1039/c3cc39291k

Reference yield: 97.0%

(S)-ethyl 1-((S)-2-((tert-butoxycarbonyl)amino)-3-phenylpropanoyl)pyrrolidine-2-carboxylate (1427166-47-9) → (S)-1-((S)-2-(ethoxycarbonyl)pyrrolidin-1-yl)-1-oxo-3-phenylpropan-2-aminium chloride (99295-22-4)

Guidance literature:

With hydrogenchloride; In 1,4-dioxane; at 25 ℃; for 1h;

DOI:10.1039/c3cc39291k

upstream raw materials:

N-tert-butoxycarbonyl-L-phenylalanine

ethyl (2S)-pyrrolidine-2-carboxylate

(S)-tert-butyl (1-(1H-benzo[d][1,2,3]triazol-1-yl)-1-oxo-3-phenylpropan-2-yl)carbamate

Downstream raw materials:

(6S,9S,12S,14aS,20S,23S,25aS)-20-benzyl-6,12-di((S)-sec-butyl)-9-(hydroxymethyl)-23-isobutylhexadecahydro-1H-dipyrrolo[1,2-a:1',2'-j][1,4,7,10,13,16,19]heptaazacyclohenicosine-5,8,11,14,19,22,25(25aH)heptaone

(S)-1-((S)-2-(ethoxycarbonyl)pyrrolidin-1-yl)-1-oxo-3-phenylpropan-2-aminium chloride

(S)-tert-butyl 2-(((S)-1-(((S)-1-((S)-2-(ethoxycarbonyl)pyrrolidin-1-yl)-1-oxo-3-phenylpropan-2-yl)amino)-4-methyl-1-oxopentan-2-yl)carbamoyl)pyrrolidine-1-carboxylate

(S)-2-(((S)-1-(((S)-1-((S)-2-(ethoxycarbonyl)pyrrolidin-1-yl)-1-oxo-3-phenylpropan-2-yl)amino)-4-methyl-1-oxopentan-2-yl)carbamoyl)pyrrolidin-1-ium chloride

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