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

Base Information

• Chemical Name: (2S,4S)-2-{[(4-Hydroxy-piperidin-1-yl)-imino-methyl]-carbamoyl}-4-tritylsulfanyl-pyrrolidine-1-carboxylic acid allyl ester
• CAS No.: 883991-81-9
• Molecular Formula: C₃₄H₃₈N₄O₄S
• Molecular Weight: 598.766
• Mol file: 883991-81-9.mol

Synonyms:

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 6 articles about (2S,4S)-2-{[(4-Hydroxy-piperidin-1-yl)-imino-methyl]-carbamoyl}-4-tritylsulfanyl-pyrrolidine-1-carboxylic acid allyl 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: 69.8%

4-HYDROXYPIPERIDINE (5382-16-1) + (2S,4S)-2-{[(imino)(pyrazol-1-yl)methyl]carbamoyl}-4-tritylthio-1-(allyloxycarbonyl)pyrrolidine (883991-68-2) → (2S,4S)-2-{[(4-Hydroxy-piperidin-1-yl)-imino-methyl]-carbamoyl}-4-tritylsulfanyl-pyrrolidine-1-carboxylic acid allyl ester (883991-81-9)

Guidance literature:

In tetrahydrofuran; Heating;

DOI:10.1016/j.ejmech.2004.12.009

Reference yield:

triphenylmethanethiol (3695-77-0) → (2S,4S)-2-{[(4-Hydroxy-piperidin-1-yl)-imino-methyl]-carbamoyl}-4-tritylsulfanyl-pyrrolidine-1-carboxylic acid allyl ester (883991-81-9)

Guidance literature:

Multi-step reaction with 4 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

4.1: 69.8 percent / tetrahydrofuran / Heating

With sodium hydroxide; chloroformic acid ethyl ester; sodium hydride; triethylamine; In tetrahydrofuran; 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-{[(4-Hydroxy-piperidin-1-yl)-imino-methyl]-carbamoyl}-4-tritylsulfanyl-pyrrolidine-1-carboxylic acid allyl ester (883991-81-9)

Guidance literature:

Multi-step reaction with 5 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

5.1: 69.8 percent / tetrahydrofuran / Heating

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

DOI:10.1016/j.ejmech.2004.12.009

upstream raw materials:

4-HYDROXYPIPERIDINE

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

triphenylmethanethiol

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