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

Base Information

• Chemical Name: (2S,4S)-2-[(2-aminoethyl)carbamoyl]-4-tritylthio-1-(allyloxycarbonyl)pyrrolidine
• CAS No.: 639457-04-8
• Molecular Formula: C₃₀H₃₃N₃O₃S
• Molecular Weight: 515.676
• Mol file: 639457-04-8.mol

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

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

There total 5 articles about (2S,4S)-2-[(2-aminoethyl)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: 86.4%

(2S,4S)-2-[(2-azidoethyl)carbamoyl]-4-tritylthio-1-(allyloxycarbonyl)pyrrolidine (639457-03-7) → (2S,4S)-2-[(2-aminoethyl)carbamoyl]-4-tritylthio-1-(allyloxycarbonyl)pyrrolidine (639457-04-8)

Guidance literature:

With water; triphenylphosphine; In tetrahydrofuran; at 40 ℃; for 4h;

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-aminoethyl)carbamoyl]-4-tritylthio-1-(allyloxycarbonyl)pyrrolidine (639457-04-8)

Guidance literature:

Multi-step reaction with 5 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

With sodium hydroxide; sodium azide; water; chloroformic acid ethyl ester; triethylamine; triphenylphosphine; In tetrahydrofuran; methanol; 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-aminoethyl)carbamoyl]-4-tritylthio-1-(allyloxycarbonyl)pyrrolidine (639457-04-8)

Guidance literature:

Multi-step reaction with 4 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

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

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

upstream raw materials:

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

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

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

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

Downstream raw materials:

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

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

C₃₉H₄₃N₅O₇S

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