(2S,3R)-3-benzyloxy-2-[2-oxo-3-(7-bromo-6-chloro-4-oxoquinazolin-3(4H)-yl)propyl]piperidine-1-carboxylic acid benzyl ester

Base Information

• Chemical Name: (2S,3R)-3-benzyloxy-2-[2-oxo-3-(7-bromo-6-chloro-4-oxoquinazolin-3(4H)-yl)propyl]piperidine-1-carboxylic acid benzyl ester
• CAS No.: 1203455-38-2
• Molecular Formula: C₃₁H₂₉BrClN₃O₅
• Molecular Weight: 638.945
• Mol file: 1203455-38-2.mol

Synonyms:(2S,3R)-3-benzyloxy-2-[2-oxo-3-(7-bromo-6-chloro-4-oxoquinazolin-3(4H)-yl)propyl]piperidine-1-carboxylic acid benzyl ester

Chemical Property of (2S,3R)-3-benzyloxy-2-[2-oxo-3-(7-bromo-6-chloro-4-oxoquinazolin-3(4H)-yl)propyl]piperidine-1-carboxylic acid benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3R)-3-benzyloxy-2-[2-oxo-3-(7-bromo-6-chloro-4-oxoquinazolin-3(4H)-yl)propyl]piperidine-1-carboxylic acid benzyl ester

There total 6 articles about (2S,3R)-3-benzyloxy-2-[2-oxo-3-(7-bromo-6-chloro-4-oxoquinazolin-3(4H)-yl)propyl]piperidine-1-carboxylic acid benzyl 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: 38.0%

4-hydroxy-6-chloro-7-bromo-quinazoline (17518-98-8) + (2S,3R)-3-benzyloxy-2-(2-oxopropyl)piperidine-1-carboxylic acid benzyl ester (1203455-36-0) → (2S,3R)-3-benzyloxy-2-[2-oxo-3-(7-bromo-6-chloro-4-oxoquinazolin-3(4H)-yl)propyl]piperidine-1-carboxylic acid benzyl ester (1203455-38-2)

Guidance literature:

(2S,3R)-3-benzyloxy-2-(2-oxopropyl)piperidine-1-carboxylic acid benzyl ester; With trimethylsilyl trifluoromethanesulfonate; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 0 ℃; for 0.75h; Inert atmosphere;

With N-Bromosuccinimide; In dichloromethane; at 20 ℃; for 3h;

4-hydroxy-6-chloro-7-bromo-quinazoline; With piperidine; potassium carbonate; In N,N-dimethyl-formamide; at 20 ℃; for 2h; Inert atmosphere;

DOI:10.1021/jo902396m

Reference yield:

4-hydroxy-6-chloro-7-bromo-quinazoline (17518-98-8) + C23H26BrNO4 → (2S,3R)-3-benzyloxy-2-[2-oxo-3-(7-bromo-6-chloro-4-oxoquinazolin-3(4H)-yl)propyl]piperidine-1-carboxylic acid benzyl ester (1203455-38-2)

Guidance literature:

With potassium carbonate; In N,N-dimethyl-formamide;

DOI:10.1016/j.tetlet.2020.152151

Reference yield:

benzyl chloroformate (501-53-1,94274-21-2) → (2S,3R)-3-benzyloxy-2-[2-oxo-3-(7-bromo-6-chloro-4-oxoquinazolin-3(4H)-yl)propyl]piperidine-1-carboxylic acid benzyl ester (1203455-38-2)

Guidance literature:

Multi-step reaction with 4 steps

1.1: triethylamine / dichloromethane / 0 °C

2.1: palladium dichloride; oxygen; copper(l) chloride / N,N-dimethyl-formamide; water

3.1: trimethylsilyl trifluoromethanesulfonate; N-ethyl-N,N-diisopropylamine / dichloromethane / 1 h / 0 °C / Inert atmosphere

3.2: 1.5 h / 0 - 20 °C / Inert atmosphere

4.1: potassium carbonate / N,N-dimethyl-formamide

With trimethylsilyl trifluoromethanesulfonate; oxygen; potassium carbonate; triethylamine; N-ethyl-N,N-diisopropylamine; copper(l) chloride; palladium dichloride; In dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1016/j.tetlet.2020.152151

upstream raw materials:

4-hydroxy-6-chloro-7-bromo-quinazoline

(2S,3R)-3-benzyloxy-2-(2-oxopropyl)piperidine-1-carboxylic acid benzyl ester

benzyl chloroformate

Downstream raw materials:

halofuginone

(-)-halofuginone didydrobromide

Refernces

• 1、 McLaughlin, Noel P.,Evans, Paul. "Dihydroxylation of vinyl sulfones: Stereoselective synthesis of (+)- and (-)-febrifugine and halofuginone". supporting information; experimental part. p. 518 - 521. Retrieved 2010/03/30.