(2S,4S)-2-{[(imino)(pyrazol-1-yl)methyl]carbamoyl}-4-tritylthio-1-(allyloxycarbonyl)pyrrolidine

Base Information

• Chemical Name: (2S,4S)-2-{[(imino)(pyrazol-1-yl)methyl]carbamoyl}-4-tritylthio-1-(allyloxycarbonyl)pyrrolidine
• CAS No.: 883991-68-2
• Molecular Formula: C₃₂H₃₁N₅O₃S
• Molecular Weight: 565.696
• Mol file: 883991-68-2.mol

Synonyms:(2S,4S)-2-{[(imino)(pyrazol-1-yl)methyl]carbamoyl}-4-tritylthio-1-(allyloxycarbonyl)pyrrolidine

Chemical Property of (2S,4S)-2-{[(imino)(pyrazol-1-yl)methyl]carbamoyl}-4-tritylthio-1-(allyloxycarbonyl)pyrrolidine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,4S)-2-{[(imino)(pyrazol-1-yl)methyl]carbamoyl}-4-tritylthio-1-(allyloxycarbonyl)pyrrolidine

There total 5 articles about (2S,4S)-2-{[(imino)(pyrazol-1-yl)methyl]carbamoyl}-4-tritylthio-1-(allyloxycarbonyl)pyrrolidine 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: 89.5%

1H-pyrazole-1-carboximidamide hydrochloride (4023-02-3) + (2S,4S)-4-tritylthio-1-(allyloxycarbonyl)pyrrolidine-2-carboxylic acid (639457-00-4) → (2S,4S)-2-{[(imino)(pyrazol-1-yl)methyl]carbamoyl}-4-tritylthio-1-(allyloxycarbonyl)pyrrolidine (883991-68-2)

Guidance literature:

(2S,4S)-4-tritylthio-1-(allyloxycarbonyl)pyrrolidine-2-carboxylic acid; With chloroformic acid ethyl ester; triethylamine; In dichloromethane; at 0 ℃; for 0.5h;

1H-pyrazole-1-carboximidamide hydrochloride; In dichloromethane; at 0 ℃; for 1h;

DOI:10.1016/j.ejmech.2004.12.009

Reference yield:

triphenylmethanethiol (3695-77-0) → (2S,4S)-2-{[(imino)(pyrazol-1-yl)methyl]carbamoyl}-4-tritylthio-1-(allyloxycarbonyl)pyrrolidine (883991-68-2)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 82.5 percent / sodium hydride / dimethylformamide; various solvent(s) / 3 h / 20 °C

2.1: 83.3 percent / NaOH / methanol / 5 h / 20 °C

3.1: ethyl chloroformate; triethylamine / CH₂Cl₂ / 0.5 h / 0 °C

3.2: 89.5 percent / CH₂Cl₂ / 1 h / 0 °C

With sodium hydroxide; chloroformic acid ethyl ester; sodium hydride; triethylamine; In methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/j.ejmech.2004.12.009

Reference yield:

methyl (2S,4R)-N-(allyloxycarbonyl)-4-hydroxypyrrolidine-2-carboxylate (126408-14-8) → (2S,4S)-2-{[(imino)(pyrazol-1-yl)methyl]carbamoyl}-4-tritylthio-1-(allyloxycarbonyl)pyrrolidine (883991-68-2)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 93.2 percent / triethylamine / CH₂Cl₂ / 1 h / 0 °C

2.1: 82.5 percent / sodium hydride / dimethylformamide; various solvent(s) / 3 h / 20 °C

3.1: 83.3 percent / NaOH / methanol / 5 h / 20 °C

4.1: ethyl chloroformate; triethylamine / CH₂Cl₂ / 0.5 h / 0 °C

4.2: 89.5 percent / CH₂Cl₂ / 1 h / 0 °C

With sodium hydroxide; chloroformic acid ethyl ester; sodium hydride; triethylamine; In methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/j.ejmech.2004.12.009

upstream raw materials:

1H-pyrazole-1-carboximidamide hydrochloride

(2S,4S)-4-tritylthio-1-(allyloxycarbonyl)pyrrolidine-2-carboxylic acid

triphenylmethanethiol

methyl (2S,4R)-N-(allyloxycarbonyl)-4-hydroxypyrrolidine-2-carboxylate

Downstream raw materials:

(2S,4S)-2-{[(5,6-Dihydro-4H-pyrimidin-1-yl)-imino-methyl]-carbamoyl}-4-tritylsulfanyl-pyrrolidine-1-carboxylic acid allyl ester

(2S,4S)-2-{[(2-Hydroxymethyl-pyrrolidin-1-yl)-imino-methyl]-carbamoyl}-4-tritylsulfanyl-pyrrolidine-1-carboxylic acid allyl ester

(2S,4S)-2-{[(4-Hydroxy-piperidin-1-yl)-imino-methyl]-carbamoyl}-4-tritylsulfanyl-pyrrolidine-1-carboxylic acid allyl ester

(2S,4S)-2-[(Imino-piperazin-1-yl-methyl)-carbamoyl]-4-tritylsulfanyl-pyrrolidine-1-carboxylic acid allyl ester