(2S,3S,4S)-N-benzoyl-4-(bromoacetyl)-2-tert-butoxycarbonyl-3-tert-butoxycarbonylmethylpyrrolidine

Base Information

• Chemical Name: (2S,3S,4S)-N-benzoyl-4-(bromoacetyl)-2-tert-butoxycarbonyl-3-tert-butoxycarbonylmethylpyrrolidine
• CAS No.: 267244-45-1
• Molecular Formula: C₂₄H₃₂BrNO₆
• Molecular Weight: 510.425
• Mol file: 267244-45-1.mol

Synonyms:(2S,3S,4S)-N-benzoyl-4-(bromoacetyl)-2-tert-butoxycarbonyl-3-tert-butoxycarbonylmethylpyrrolidine

Chemical Property of (2S,3S,4S)-N-benzoyl-4-(bromoacetyl)-2-tert-butoxycarbonyl-3-tert-butoxycarbonylmethylpyrrolidine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3S,4S)-N-benzoyl-4-(bromoacetyl)-2-tert-butoxycarbonyl-3-tert-butoxycarbonylmethylpyrrolidine

There total 5 articles about (2S,3S,4S)-N-benzoyl-4-(bromoacetyl)-2-tert-butoxycarbonyl-3-tert-butoxycarbonylmethylpyrrolidine 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: 93.0%

(2S,3S,4S)-acetyl-N-benzoyl-2-tert-butoxycarbonyl-3-tert-butoxycarbonylmethyl-4-pyrrolidine (267244-44-0) → (2S,3S,4S)-N-benzoyl-4-(bromoacetyl)-2-tert-butoxycarbonyl-3-tert-butoxycarbonylmethylpyrrolidine (267244-45-1)

Guidance literature:

(2S,3S,4S)-acetyl-N-benzoyl-2-tert-butoxycarbonyl-3-tert-butoxycarbonylmethyl-4-pyrrolidine; With chloro-trimethyl-silane; lithium hexamethyldisilazane; at -78 ℃;

With phenyltrimethylammonium tribromide; at -78 - 20 ℃;

DOI:10.1016/S0960-894X(99)00690-3

Reference yield:

1-benzoyl-3-tert-butoxycarbonylmethyl-4-(1-trimethylsilanyloxy-vinyl)-pyrrolidine-2-carboxylic acid tert-butyl ester (1028273-72-4) → (2S,3S,4S)-N-benzoyl-4-(bromoacetyl)-2-tert-butoxycarbonyl-3-tert-butoxycarbonylmethylpyrrolidine (267244-45-1)

Guidance literature:

With phenyltrimethylammonium tribromide; In tetrahydrofuran; at 0 ℃; for 0.5h;

DOI:10.1021/jo000846l

Reference yield:

benzoyl chloride (98-88-4) → (2S,3S,4S)-N-benzoyl-4-(bromoacetyl)-2-tert-butoxycarbonyl-3-tert-butoxycarbonylmethylpyrrolidine (267244-45-1)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 455 mg / NaOH / H₂O; dioxane / 22 h / 20 °C

2.1: O₃ / CH₂Cl₂; methanol / 0.75 h / -78 °C

2.2: 99 percent / Ph₃P / CH₂Cl₂; methanol / 1 h / 20 °C

3.1: lithium hexamethyldisilylamide / tetrahydrofuran / 0.42 h / -78 °C

4.1: 115 mg / phenyltrimethylammonium tribromide / tetrahydrofuran / 0.5 h / 0 °C

With sodium hydroxide; phenyltrimethylammonium tribromide; ozone; lithium hexamethyldisilazane; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; water;

DOI:10.1021/jo000846l

upstream raw materials:

(2S,3S,4S)-acetyl-N-benzoyl-2-tert-butoxycarbonyl-3-tert-butoxycarbonylmethyl-4-pyrrolidine

1-benzoyl-3-tert-butoxycarbonylmethyl-4-(1-trimethylsilanyloxy-vinyl)-pyrrolidine-2-carboxylic acid tert-butyl ester

benzoyl chloride

(2S,3S,4S)-N-benzoyl-2-tert-butoxycarbonyl-3-tert-butoxycarbonylmethyl-4-isopropylidenylpyrrolidine

Downstream raw materials:

(2S,3S,4S)-N-benzoyl-2-tert-butoxycarbonyl-3-tert-butoxycarbonylmethyl-4-(2'-methylthiazol-4'-yl)pyrrolidine

(2S,3S,4S)-N-benzoyl-2-tert-butoxycarbonyl-3-tert-butoxycarbonylmethyl-4-(2'-(methylamino)thiazol-4'-yl)pyrrolidine

(2S,3S,4S)-4-(2'-aminothiazol-4'-yl)-N-benzoyl-2-tert-butoxycarbonyl-3-tert-butoxycarbonylmethylpyrrolidine

(2S,3S,4S)-N-benzoyl-2-tert-butoxycarbonyl-3-tert-butoxycarbonylmethyl-4-(2'-phenylthiazol-4'-yl)pyrrolidine