1-[[5-oxo-1-(phenylmethyl)-(2S)-pyrrolidinyl]methyl]-1H-imidazole-5-carboxylic acid

Base Information

Chemical Name:1-[[5-oxo-1-(phenylmethyl)-(2S)-pyrrolidinyl]methyl]-1H-imidazole-5-carboxylic acid
CAS No.:1308719-43-8
Molecular Formula:C₁₆H₁₇N₃O₃
Molecular Weight:299.329
Hs Code.:

Synonyms:1-[[5-oxo-1-(phenylmethyl)-(2S)-pyrrolidinyl]methyl]-1H-imidazole-5-carboxylic acid

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Chemical Property of 1-[[5-oxo-1-(phenylmethyl)-(2S)-pyrrolidinyl]methyl]-1H-imidazole-5-carboxylic acid

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Technology Process of 1-[[5-oxo-1-(phenylmethyl)-(2S)-pyrrolidinyl]methyl]-1H-imidazole-5-carboxylic acid

There total 4 articles about 1-[[5-oxo-1-(phenylmethyl)-(2S)-pyrrolidinyl]methyl]-1H-imidazole-5-carboxylic acid 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%

: 1H-imidazole-4-carboxylic acid phenylmethyl ester lithium salt

: 132991-79-8
4-methylbenzenesulfonic acid [5-oxo-1-(phenylmethyl)-(2S)-pyrrolidinyl]methyl ester

: 1-[[5-oxo-1-(phenylmethyl)-(2S)-pyrrolidinyl]methyl]-1H-imidazole-4-carboxylic acid

: 1308719-43-8
1-[[5-oxo-1-(phenylmethyl)-(2S)-pyrrolidinyl]methyl]-1H-imidazole-5-carboxylic acid

Guidance literature:: 1H-imidazole-4-carboxylic acid phenylmethyl ester lithium salt; 4-methylbenzenesulfonic acid [5-oxo-1-(phenylmethyl)-(2S)-pyrrolidinyl]methyl ester; In N,N-dimethyl-formamide; at 50 ℃; Inert atmosphere;

With palladium 10% on activated carbon; hydrogen; In methanol;
DOI:10.1016/j.bmc.2011.03.044

Reference yield:

: 103301-78-6,143317-59-3,57171-00-3
methyl (2S)-1-benzyl-5-pyrrolidone-2-carboxylate

: 1-[[5-oxo-1-(phenylmethyl)-(2S)-pyrrolidinyl]methyl]-1H-imidazole-4-carboxylic acid

: 1308719-43-8
1-[[5-oxo-1-(phenylmethyl)-(2S)-pyrrolidinyl]methyl]-1H-imidazole-5-carboxylic acid

Guidance literature:: Multi-step reaction with 3 steps

1.1: lithium borohydride / tetrahydrofuran / 20 °C / Inert atmosphere

1.2: 0 °C / Inert atmosphere

2.1: triethylamine / dichloromethane / 0 - 20 °C

3.1: N,N-dimethyl-formamide / 50 °C / Inert atmosphere

With lithium borohydride; triethylamine; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/j.bmc.2011.03.044

Reference yield:

: 98-79-3
L-Pyroglutamic acid

: 1-[[5-oxo-1-(phenylmethyl)-(2S)-pyrrolidinyl]methyl]-1H-imidazole-4-carboxylic acid

: 1308719-43-8
1-[[5-oxo-1-(phenylmethyl)-(2S)-pyrrolidinyl]methyl]-1H-imidazole-5-carboxylic acid

Guidance literature:: Multi-step reaction with 5 steps

1.1: thionyl chloride

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

3.1: lithium borohydride / tetrahydrofuran / 20 °C / Inert atmosphere

3.2: 0 °C / Inert atmosphere

4.1: triethylamine / dichloromethane / 0 - 20 °C

5.1: N,N-dimethyl-formamide / 50 °C / Inert atmosphere

With lithium borohydride; thionyl chloride; sodium hydride; triethylamine; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; paraffin oil;
DOI:10.1016/j.bmc.2011.03.044