methyl (2S,5R)-6-(benzyloxy)-7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carboxylate

Base Information

• Chemical Name: methyl (2S,5R)-6-(benzyloxy)-7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carboxylate
• CAS No.: 1416134-63-8
• Molecular Formula: C₁₆H₂₀N₂O₄
• Molecular Weight: 304.346
• Mol file: 1416134-63-8.mol

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

Chemical Property of methyl (2S,5R)-6-(benzyloxy)-7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carboxylate

Chemical Property:

Purity/Quality:

97% ^*data from raw suppliers

ethyl(2S,5R)-6-(benzyloxy)-7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carboxylate 95+% ^*data from reagent suppliers

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Technology Process of methyl (2S,5R)-6-(benzyloxy)-7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carboxylate

There total 25 articles about methyl (2S,5R)-6-(benzyloxy)-7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carboxylate 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: 92.0%

bis(trichloromethyl) carbonate (32315-10-9) + (2S,5R)?5?[(benzyloxy)amino]piperidine?2?carboxylate (1416134-47-8) → (2S,5R)-6-(benzyloxy)-7-oxo-1,6-diazabicyclo[3.2.1]octan-2-carboxylic acid ethyl ester (1416134-63-8)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 0 - 20 ℃; for 16h;

DOI:10.1021/acs.jmedchem.0c01535

Reference yield: 85.0%

bis(trichloromethyl) carbonate (32315-10-9) + (2S,5R)-5-(benzyloxyamino)piperidin-1,2-dicarboxylic acid 1-tert-butyl ester 2-ethyl ester (1463501-46-3) → (2S,5R)-6-(benzyloxy)-7-oxo-1,6-diazabicyclo[3.2.1]octan-2-carboxylic acid ethyl ester (1416134-63-8)

Guidance literature:

bis(trichloromethyl) carbonate; (2S,5R)-5-(benzyloxyamino)piperidin-1,2-dicarboxylic acid 1-tert-butyl ester 2-ethyl ester; With N-ethyl-N,N-diisopropylamine; In dichloromethane; for 0.5h; Cooling with ice;

With methanesulfonic acid; for 0.0833333h; Cooling with ice;

With potassium hydrogencarbonate; In water; for 0.5h; Cooling with ice;

Reference yield:

(2S,5R)-5-hydroxypiperidine-2-carboxylic acid (63088-78-8,448964-01-0,478409-64-2) → (2S,5R)-6-(benzyloxy)-7-oxo-1,6-diazabicyclo[3.2.1]octan-2-carboxylic acid ethyl ester (1416134-63-8)

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

7.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.5 h / Cooling with ice

7.2: 0.08 h / Cooling with ice

7.3: 0.5 h / 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;

upstream raw materials:

bis(trichloromethyl) carbonate

ethyl (2S,5R)-5-[(benzyloxy)amino]piperidine-2-carboxylate oxalic acid salt

(2S)-5-(benzyloxyimino)-piperidine-2-carboxylic acid benzyl ester

(2S)-5-benzyloxyaminopiperidin-2-carboxylic acid benzyl ester oxalic acid salt

Downstream raw materials:

(2S,5R)-2-carbamoyl-7-oxo-1,6-diazabicylco[3.2.1]octan-6-yl hydrogensulfate

(1R,2S,5R)-6-(benzyloxy)-7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carboxamide

(2S,5R)-1,6-diazabicyclo[3.2.1]octane-2-carboxamide 7-oxo-6-(sulfoxy)monosodium salt

({[(2S,5R)-2-carbamoyl-7-oxo-6-(sulfooxy)-1,6-diazabicyclo[3,2,1]-oct-6-yl]oxy}sulfonyl)tetrabutylammonium salt

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