4-{(S)-4-carboxy-2-[(5-{2-[(S)-2-(cyclobutyl-methyl-carbamoyl)-pyrrolidin-1-yl]-2-oxo-ethoxy}-1-phenyl-1H-pyrazole-3-carbonyl)-amino]-butyryl}-piperazine-1-carboxylic acid ethyl ester

Base Information

• Chemical Name: 4-{(S)-4-carboxy-2-[(5-{2-[(S)-2-(cyclobutyl-methyl-carbamoyl)-pyrrolidin-1-yl]-2-oxo-ethoxy}-1-phenyl-1H-pyrazole-3-carbonyl)-amino]-butyryl}-piperazine-1-carboxylic acid ethyl ester
• CAS No.: 1163790-92-8
• Molecular Formula: C₃₄H₄₅N₇O₉
• Molecular Weight: 695.773
• Mol file: 1163790-92-8.mol

Synonyms:

Chemical Property of 4-{(S)-4-carboxy-2-[(5-{2-[(S)-2-(cyclobutyl-methyl-carbamoyl)-pyrrolidin-1-yl]-2-oxo-ethoxy}-1-phenyl-1H-pyrazole-3-carbonyl)-amino]-butyryl}-piperazine-1-carboxylic acid ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-{(S)-4-carboxy-2-[(5-{2-[(S)-2-(cyclobutyl-methyl-carbamoyl)-pyrrolidin-1-yl]-2-oxo-ethoxy}-1-phenyl-1H-pyrazole-3-carbonyl)-amino]-butyryl}-piperazine-1-carboxylic acid ethyl ester

There total 6 articles about 4-{(S)-4-carboxy-2-[(5-{2-[(S)-2-(cyclobutyl-methyl-carbamoyl)-pyrrolidin-1-yl]-2-oxo-ethoxy}-1-phenyl-1H-pyrazole-3-carbonyl)-amino]-butyryl}-piperazine-1-carboxylic acid ethyl ester 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: 17.0%

4-[(S)-4-tert-butoxycarbonyl-2-({5-[2-((S)-2-carboxy-pyrrolidin-1-yl)-2-oxoethoxy]-1-phenyl-1H-pyrazole-3-carbonyl}amino)butyryl]piperazine-1-carboxylic acid ethyl ester (1163790-69-9) + N-methylcyclobutanamine hydrochloride (848497-98-3) → 4-{(S)-4-carboxy-2-[(5-{2-[(S)-2-(cyclobutyl-methyl-carbamoyl)-pyrrolidin-1-yl]-2-oxo-ethoxy}-1-phenyl-1H-pyrazole-3-carbonyl)-amino]-butyryl}-piperazine-1-carboxylic acid ethyl ester (1163790-92-8)

Guidance literature:

4-[(S)-4-tert-butoxycarbonyl-2-({5-[2-((S)-2-carboxy-pyrrolidin-1-yl)-2-oxoethoxy]-1-phenyl-1H-pyrazole-3-carbonyl}amino)butyryl]piperazine-1-carboxylic acid ethyl ester; With benzotriazol-1-ol; 1,2-dichloro-ethane; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; for 0.333333h;

N-methylcyclobutanamine hydrochloride; In N,N-dimethyl-formamide; for 12h;

With trifluoroacetic acid; In dichloromethane; for 12h;

DOI:10.1021/jm300771j

Reference yield:

4-[(S)-2-({5-[2-((S)-2-benzyloxycarbonyl-pyrrolidin-1-yl)-2-oxoethoxy]-1-phenyl-1H-pyrazole-3-carbonyl}amino)-4-tert-butoxycarbonylbutyryl]piperazine-1-carboxylic acid ethyl ester (1163790-68-8) → 4-{(S)-4-carboxy-2-[(5-{2-[(S)-2-(cyclobutyl-methyl-carbamoyl)-pyrrolidin-1-yl]-2-oxo-ethoxy}-1-phenyl-1H-pyrazole-3-carbonyl)-amino]-butyryl}-piperazine-1-carboxylic acid ethyl ester (1163790-92-8)

Guidance literature:

Multi-step reaction with 2 steps

1.1: palladium 10% on activated carbon; hydrogen / ethyl acetate / 24 h / 2250.23 Torr / Inert atmosphere

2.1: benzotriazol-1-ol; 1,2-dichloro-ethane; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 0.33 h

2.2: 12 h

2.3: 12 h

With palladium 10% on activated carbon; hydrogen; benzotriazol-1-ol; 1,2-dichloro-ethane; N-ethyl-N,N-diisopropylamine; In ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1021/jm300771j

Reference yield:

4-((S)-2-amino-4-tert-butoxycarbonyl-butyryl)piperazine-1-carboxylic acid ethyl ester (710335-28-7) → 4-{(S)-4-carboxy-2-[(5-{2-[(S)-2-(cyclobutyl-methyl-carbamoyl)-pyrrolidin-1-yl]-2-oxo-ethoxy}-1-phenyl-1H-pyrazole-3-carbonyl)-amino]-butyryl}-piperazine-1-carboxylic acid ethyl ester (1163790-92-8)

Guidance literature:

Multi-step reaction with 7 steps

1.1: benzotriazol-1-ol; 1,2-dichloro-ethane / N,N-dimethyl-formamide / 12 h / 20 °C

2.1: trifluoroacetic acid / dichloromethane / 4 h

3.1: caesium carbonate / N,N-dimethyl-formamide / 12 h / 20 °C

4.1: palladium 10% on activated carbon; hydrogen / ethyl acetate / 16 h / 2250.23 Torr / Inert atmosphere

5.1: benzotriazol-1-ol; 1,2-dichloro-ethane; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 12 h / 0 - 20 °C

6.1: palladium 10% on activated carbon; hydrogen / ethyl acetate / 24 h / 2250.23 Torr / Inert atmosphere

7.1: benzotriazol-1-ol; 1,2-dichloro-ethane; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 0.33 h

7.2: 12 h

7.3: 12 h

With palladium 10% on activated carbon; hydrogen; benzotriazol-1-ol; caesium carbonate; 1,2-dichloro-ethane; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; In dichloromethane; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1021/jm300771j

upstream raw materials:

4-[(S)-2-({5-[2-((S)-2-benzyloxycarbonyl-pyrrolidin-1-yl)-2-oxoethoxy]-1-phenyl-1H-pyrazole-3-carbonyl}amino)-4-tert-butoxycarbonylbutyryl]piperazine-1-carboxylic acid ethyl ester

4-[(S)-4-tert-butoxycarbonyl-2-({5-[2-((S)-2-carboxy-pyrrolidin-1-yl)-2-oxoethoxy]-1-phenyl-1H-pyrazole-3-carbonyl}amino)butyryl]piperazine-1-carboxylic acid ethyl ester

N-methylcyclobutanamine hydrochloride

C₂₂H₂₇N₅O₇