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

Base Information

Chemical Name:(2S,3R)-3-benzyloxy-2-[2-oxo-3-(4-oxoquinazolin-3(4H)-yl)propyl]piperidine-1-carboxylic acid benzyl ester
CAS No.:1203455-37-1
Molecular Formula:C₃₁H₃₁N₃O₅
Molecular Weight:525.604
Hs Code.:

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

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

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Technology Process of (2S,3R)-3-benzyloxy-2-[2-oxo-3-(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-(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: 47.0%

: 1203455-36-0
(2S,3R)-3-benzyloxy-2-(2-oxopropyl)piperidine-1-carboxylic acid benzyl ester

: 491-36-1,134434-33-6
4-quinazolinol

: 1203455-37-1
(2S,3R)-3-benzyloxy-2-[2-oxo-3-(4-oxoquinazolin-3(4H)-yl)propyl]piperidine-1-carboxylic acid benzyl ester

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-quinazolinol; With piperidine; potassium carbonate; In N,N-dimethyl-formamide; at 20 ℃; for 2h; Inert atmosphere;
DOI:10.1021/jo902396m

Reference yield:

: C₂₃H₂₆BrNO₄

: 491-36-1,134434-33-6
4-quinazolinol

: 1203455-37-1
(2S,3R)-3-benzyloxy-2-[2-oxo-3-(4-oxoquinazolin-3(4H)-yl)propyl]piperidine-1-carboxylic acid benzyl ester

Guidance literature:: With potassium carbonate; In N,N-dimethyl-formamide; at 20 ℃; for 16h;
DOI:10.1016/j.tetlet.2020.152151

Reference yield:

: 501-53-1,94274-21-2
benzyl chloroformate

: 1203455-37-1
(2S,3R)-3-benzyloxy-2-[2-oxo-3-(4-oxoquinazolin-3(4H)-yl)propyl]piperidine-1-carboxylic acid benzyl ester

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 / 16 h / 20 °C

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