(2S,4S)-2-(2-{[(E)-Allyloxycarbonylimino-methyl]-amino}-ethylcarbamoyl)-4-tritylsulfanyl-pyrrolidine-1-carboxylic acid allyl ester

Base Information

• Chemical Name: (2S,4S)-2-(2-{[(E)-Allyloxycarbonylimino-methyl]-amino}-ethylcarbamoyl)-4-tritylsulfanyl-pyrrolidine-1-carboxylic acid allyl ester
• CAS No.: 639457-21-9
• Molecular Formula: C₃₅H₃₈N₄O₅S
• Molecular Weight: 626.777
• Mol file: 639457-21-9.mol

Synonyms:(2S,4S)-2-(2-{[(E)-Allyloxycarbonylimino-methyl]-amino}-ethylcarbamoyl)-4-tritylsulfanyl-pyrrolidine-1-carboxylic acid allyl ester

Chemical Property of (2S,4S)-2-(2-{[(E)-Allyloxycarbonylimino-methyl]-amino}-ethylcarbamoyl)-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-(2-{[(E)-Allyloxycarbonylimino-methyl]-amino}-ethylcarbamoyl)-4-tritylsulfanyl-pyrrolidine-1-carboxylic acid allyl ester

There total 6 articles about (2S,4S)-2-(2-{[(E)-Allyloxycarbonylimino-methyl]-amino}-ethylcarbamoyl)-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: 79.8%

ethyl formimidate hydrochloride (16694-46-5) + Allyl chloroformate (2937-50-0) + (2S,4S)-2-[(2-aminoethyl)carbamoyl]-4-tritylthio-1-(allyloxycarbonyl)pyrrolidine (639457-04-8) → (2S,4S)-2-(2-{[(E)-Allyloxycarbonylimino-methyl]-amino}-ethylcarbamoyl)-4-tritylsulfanyl-pyrrolidine-1-carboxylic acid allyl ester (639457-21-9)

Guidance literature:

ethyl formimidate hydrochloride; (2S,4S)-2-[(2-aminoethyl)carbamoyl]-4-tritylthio-1-(allyloxycarbonyl)pyrrolidine; In ethanol; for 3h; Heating;

Allyl chloroformate; With triethylamine; In dichloromethane; at 0 ℃; for 1h;

DOI:10.1016/S0223-5234(03)00143-0

Reference yield:

(2S,4S)-4-tritylthio-1-(allyloxycarbonyl)pyrrolidine-2-carboxylic acid methyl ester (625388-36-5) → (2S,4S)-2-(2-{[(E)-Allyloxycarbonylimino-methyl]-amino}-ethylcarbamoyl)-4-tritylsulfanyl-pyrrolidine-1-carboxylic acid allyl ester (639457-21-9)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 83.2 percent / NaOH / methanol / 5 h / 20 °C

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

2.2: 89.5 percent / CH₂Cl₂ / 1 h / 0 °C

3.1: 91.7 percent / triethylamine / CH₂Cl₂ / 1 h / 0 °C

4.1: 85.4 percent / sodium azide / dimethylsulfoxide / 5 h / 70 °C

5.1: 86.4 percent / triphenylphosphine; H₂O / tetrahydrofuran / 4 h / 40 °C

6.1: ethanol / 3 h / Heating

6.2: 79.8 percent / triethylamine / CH₂Cl₂ / 1 h / 0 °C

With sodium hydroxide; sodium azide; water; chloroformic acid ethyl ester; triethylamine; triphenylphosphine; In tetrahydrofuran; methanol; ethanol; dichloromethane; dimethyl sulfoxide;

DOI:10.1016/S0223-5234(03)00143-0

Reference yield:

(2S,4S)-4-tritylthio-1-(allyloxycarbonyl)pyrrolidine-2-carboxylic acid (639457-00-4) → (2S,4S)-2-(2-{[(E)-Allyloxycarbonylimino-methyl]-amino}-ethylcarbamoyl)-4-tritylsulfanyl-pyrrolidine-1-carboxylic acid allyl ester (639457-21-9)

Guidance literature:

Multi-step reaction with 5 steps

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

1.2: 89.5 percent / CH₂Cl₂ / 1 h / 0 °C

2.1: 91.7 percent / triethylamine / CH₂Cl₂ / 1 h / 0 °C

3.1: 85.4 percent / sodium azide / dimethylsulfoxide / 5 h / 70 °C

4.1: 86.4 percent / triphenylphosphine; H₂O / tetrahydrofuran / 4 h / 40 °C

5.1: ethanol / 3 h / Heating

5.2: 79.8 percent / triethylamine / CH₂Cl₂ / 1 h / 0 °C

With sodium azide; water; chloroformic acid ethyl ester; triethylamine; triphenylphosphine; In tetrahydrofuran; ethanol; dichloromethane; dimethyl sulfoxide;

DOI:10.1016/S0223-5234(03)00143-0

upstream raw materials:

ethyl formimidate hydrochloride

Allyl chloroformate

(2S,4S)-2-[(2-aminoethyl)carbamoyl]-4-tritylthio-1-(allyloxycarbonyl)pyrrolidine

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