(2S,5R)-6-(benzyloxy)-7-oxo-1,6-diazabicyclo[3.2.1]octan-2-carboxylic acid allyl ester

Base Information

Chemical Name:(2S,5R)-6-(benzyloxy)-7-oxo-1,6-diazabicyclo[3.2.1]octan-2-carboxylic acid allyl ester
CAS No.:1383814-59-2
Molecular Formula:C₁₇H₂₀N₂O₄
Molecular Weight:316.357
Hs Code.:

Synonyms:(2S,5R)-6-(benzyloxy)-7-oxo-1,6-diazabicyclo[3.2.1]octan-2-carboxylic acid allyl ester

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Chemical Property of (2S,5R)-6-(benzyloxy)-7-oxo-1,6-diazabicyclo[3.2.1]octan-2-carboxylic acid allyl ester

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Technology Process of (2S,5R)-6-(benzyloxy)-7-oxo-1,6-diazabicyclo[3.2.1]octan-2-carboxylic acid allyl ester

There total 12 articles about (2S,5R)-6-(benzyloxy)-7-oxo-1,6-diazabicyclo[3.2.1]octan-2-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: 14.0%

: 1174020-25-7,2064219-13-0
(2S,5R)-6-(benzyloxy)-7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carboxylic acid

: 106-95-6
allyl bromide

: 1383814-59-2
(2S,5R)-6-(benzyloxy)-7-oxo-1,6-diazabicyclo[3.2.1]octan-2-carboxylic acid allyl ester

Guidance literature:: With sodium hydrogencarbonate; In N,N-dimethyl-formamide; for 6.5h;

Reference yield: 12.0%

: 32315-10-9
bis(trichloromethyl) carbonate

: (2S,5R)-5-(benzyloxyamino)piperidin-1,2-dicarboxylic acid 2-allyl ester 1-tert-butyl ester

: 1383814-59-2
(2S,5R)-6-(benzyloxy)-7-oxo-1,6-diazabicyclo[3.2.1]octan-2-carboxylic acid allyl ester

Guidance literature:: bis(trichloromethyl) carbonate; (2S,5R)-5-(benzyloxyamino)piperidin-1,2-dicarboxylic acid 2-allyl ester 1-tert-butyl ester; With N-ethyl-N,N-diisopropylamine; In dichloromethane; for 0.333333h; Cooling with ice;

With methanesulfonic acid; for 0.666667h; Cooling with ice;

With potassium hydrogencarbonate; In water; Cooling with ice;

Reference yield:

: 63088-78-8,448964-01-0,478409-64-2
(2S,5R)-5-hydroxypiperidine-2-carboxylic acid

: 1383814-59-2
(2S,5R)-6-(benzyloxy)-7-oxo-1,6-diazabicyclo[3.2.1]octan-2-carboxylic acid allyl ester

Guidance literature:: Multi-step reaction with 7 steps

1.1: hydrogenchloride / 3 h / 63 - 67 °C

2.1: triethylamine / ethyl acetate / 0.5 h / -40 - -12 °C

2.2: 1.5 h / -2 °C

3.1: 2,6-dimethylpyridine / acetonitrile / 0.17 h / -43 - -37 °C

3.2: 0.83 h / -35 °C

3.3: 40 h / -5 - 5 °C

4.1: hydrogenchloride / methanol / 27 h / Reflux

5.1: sodium hydroxide / water; 1,4-dioxane / 1 h / Cooling with ice

5.2: 20 °C

6.1: N-ethyl-N,N-diisopropylamine / acetonitrile / 20 °C / Cooling with ice

7.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.33 h / Cooling with ice

7.2: 0.67 h / Cooling with ice

7.3: Cooling with ice

With 2,6-dimethylpyridine; hydrogenchloride; triethylamine; N-ethyl-N,N-diisopropylamine; sodium hydroxide; In 1,4-dioxane; methanol; dichloromethane; water; ethyl acetate; acetonitrile;