methyl 1-[((2S)-1-4-[(benzyloxy)carbonyl]benzyl-5-oxotetrahydro-1H-pyrrol-2-yl)methyl]-1H-imidazole-4-carboxylate

Base Information

• Chemical Name: methyl 1-[((2S)-1-4-[(benzyloxy)carbonyl]benzyl-5-oxotetrahydro-1H-pyrrol-2-yl)methyl]-1H-imidazole-4-carboxylate
• CAS No.: 1308719-82-5
• Molecular Formula: C₂₅H₂₅N₃O₅
• Molecular Weight: 447.491

Synonyms:methyl 1-[((2S)-1-4-[(benzyloxy)carbonyl]benzyl-5-oxotetrahydro-1H-pyrrol-2-yl)methyl]-1H-imidazole-4-carboxylate

Chemical Property of methyl 1-[((2S)-1-4-[(benzyloxy)carbonyl]benzyl-5-oxotetrahydro-1H-pyrrol-2-yl)methyl]-1H-imidazole-4-carboxylate

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Technology Process of methyl 1-[((2S)-1-4-[(benzyloxy)carbonyl]benzyl-5-oxotetrahydro-1H-pyrrol-2-yl)methyl]-1H-imidazole-4-carboxylate

There total 9 articles about methyl 1-[((2S)-1-4-[(benzyloxy)carbonyl]benzyl-5-oxotetrahydro-1H-pyrrol-2-yl)methyl]-1H-imidazole-4-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: 38.0%

4-[[(2S)-[[[(4-methylphenyl)sulfonyl]oxy]methyl]-5-oxo-1-pyrrolidinyl]methyl]benzoic acid phenylmethyl ester (1308719-60-9) + Methyl imidazole-4-carboxylate (17325-26-7) → methyl 1-[((2S)-1-4-[(benzyloxy)carbonyl]benzyl-5-oxotetrahydro-1H-pyrrol-2-yl)methyl]-1H-imidazole-4-carboxylate (1308719-82-5) + methyl 1-[((2S)-1-4-[(benzyloxy)carbonyl]benzyl-5-oxotetrahydro-1H-pyrrol-2-yl)methyl]-1H-imidazole-5-carboxylate (1308719-69-8)

Guidance literature:

Methyl imidazole-4-carboxylate; With caesium carbonate; In N,N-dimethyl-formamide; at 50 ℃; for 0.5h; Inert atmosphere;

4-[[(2S)-[[[(4-methylphenyl)sulfonyl]oxy]methyl]-5-oxo-1-pyrrolidinyl]methyl]benzoic acid phenylmethyl ester; In N,N-dimethyl-formamide; at 50 ℃; Inert atmosphere;

DOI:10.1016/j.bmc.2011.03.044

Reference yield:

(S)-Pyroglutaminol (17342-08-4) → methyl 1-[((2S)-1-4-[(benzyloxy)carbonyl]benzyl-5-oxotetrahydro-1H-pyrrol-2-yl)methyl]-1H-imidazole-4-carboxylate (1308719-82-5) + methyl 1-[((2S)-1-4-[(benzyloxy)carbonyl]benzyl-5-oxotetrahydro-1H-pyrrol-2-yl)methyl]-1H-imidazole-5-carboxylate (1308719-69-8)

Guidance literature:

Multi-step reaction with 5 steps

1.1: dmap; triethylamine / N,N-dimethyl-formamide / 2.5 h / 20 °C

2.1: sodium hydride / tetrahydrofuran; paraffin oil / 0 - 20 °C

3.1: trifluoroacetic acid / dichloromethane / 0.17 h / 20 °C

4.1: triethylamine / dichloromethane / 0 - 20 °C

5.1: caesium carbonate / N,N-dimethyl-formamide / 0.5 h / 50 °C / Inert atmosphere

5.2: 50 °C / Inert atmosphere

With dmap; sodium hydride; caesium carbonate; triethylamine; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; paraffin oil;

DOI:10.1016/j.bmc.2011.03.044

Reference yield:

4-[[2-oxo-(5S)-[[(triethylsilyl)oxy]methyl]-1-pyrrolidinyl]methyl]benzoic acid phenylmethyl ester (1308719-52-9) → methyl 1-[((2S)-1-4-[(benzyloxy)carbonyl]benzyl-5-oxotetrahydro-1H-pyrrol-2-yl)methyl]-1H-imidazole-4-carboxylate (1308719-82-5) + methyl 1-[((2S)-1-4-[(benzyloxy)carbonyl]benzyl-5-oxotetrahydro-1H-pyrrol-2-yl)methyl]-1H-imidazole-5-carboxylate (1308719-69-8)

Guidance literature:

Multi-step reaction with 3 steps

1.1: trifluoroacetic acid / dichloromethane / 0.17 h / 20 °C

2.1: triethylamine / dichloromethane / 0 - 20 °C

3.1: caesium carbonate / N,N-dimethyl-formamide / 0.5 h / 50 °C / Inert atmosphere

3.2: 50 °C / Inert atmosphere

With caesium carbonate; triethylamine; trifluoroacetic acid; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/j.bmc.2011.03.044

upstream raw materials:

(5S)-[[(triethylsilyl)oxy]methyl]-2-pyrrolidinone

4-[[2-oxo-(5S)-[[(triethylsilyl)oxy]methyl]-1-pyrrolidinyl]methyl]benzoic acid phenylmethyl ester

4-[[(2S)-(hydroxymethyl)-5-oxo-1-pyrrolidinyl]methyl]benzoic acid phenylmethyl ester

4-[[(2S)-[[[(4-methylphenyl)sulfonyl]oxy]methyl]-5-oxo-1-pyrrolidinyl]methyl]benzoic acid phenylmethyl ester

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