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

Base Information

• Chemical Name: (2S,5R)-2-carbamoyl-7-oxo-1,6-diazabicyclo[3.2.1]octan-6-yl sulfate
• CAS No.: 1174020-64-4
• Molecular Formula: C₁₇H₂₈N₄O₅
• Molecular Weight: 368.433
• Mol file: 1174020-64-4.mol

Synonyms:tert-butyl 4-((2S,5R)-6-hydroxy-7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carboxamido)piperidine-1-carboxylate hydrate

Chemical Property of (2S,5R)-2-carbamoyl-7-oxo-1,6-diazabicyclo[3.2.1]octan-6-yl sulfate

Chemical Property:

• PKA: 10.28±0.40(Predicted)
• Density: 1.33±0.1 g/cm3(Predicted)
• Storage Temp.: 2-8°C

Purity/Quality:

98% ^*data from raw suppliers

tert-Butyl4-((1R,2S,5R)-6-hydroxy-7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carboxamido)piperidine-1-carboxylate 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,5R)-2-carbamoyl-7-oxo-1,6-diazabicyclo[3.2.1]octan-6-yl sulfate

There total 1 articles about (2S,5R)-2-carbamoyl-7-oxo-1,6-diazabicyclo[3.2.1]octan-6-yl sulfate 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:

(2S,5R)-5-hydroxypiperidine-2-carboxylic acid (63088-78-8,448964-01-0,478409-64-2) → tert-butyl 4-((2S,5R)-6-hydroxy-7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carboxamido)piperidine-1-carboxylate hydrate (1174020-64-4)

Guidance literature:

Multi-step reaction with 8 steps

1: sodium hydroxide / water; acetone / 23 - 30 °C / pH 10.2 - 10.7 / Inert atmosphere

2: 2-Nitrobenzenesulfonyl chloride; triethylamine / acetone; ethyl acetate / 20 - 28 °C / Inert atmosphere

3: tetrahydrofuran / 0.18 h / 72 °C / Inert atmosphere

4: dmap / tetrahydrofuran / 20 - 30 °C / Inert atmosphere

5: potassium carbonate / N,N-dimethyl acetamide / 60 - 70 °C / Inert atmosphere

6: lithium hydroxide / methanol / 50 °C

7: N-ethyl-N,N-diisopropylamine / dichloromethane / -18 - 0 °C / Inert atmosphere

8: hydrogen / tetrahydrofuran / 20 h / 23 °C / 3087.28 Torr

With dmap; hydrogen; potassium carbonate; 2-Nitrobenzenesulfonyl chloride; triethylamine; N-ethyl-N,N-diisopropylamine; sodium hydroxide; lithium hydroxide; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl acetamide; water; ethyl acetate; acetone;

DOI:10.1021/ol4031606

Reference yield:

tert-butyl 4-((2S,5R)-6-hydroxy-7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carboxamido)piperidine-1-carboxylate hydrate (1174020-64-4) + phenylcarbonochloridothioate (1005-56-7) → tert-butyl 4-[({(2S,5R)-7-oxo-6-[(phenoxycarbonothioyl)oxy]-1,6-diazabicyclo[3.2.1]oct-2-yl}carbonyl)amino]piperidine-1-carboxylate (1174020-94-0)

Guidance literature:

With pyridine; dmap; In dichloromethane; at 20 ℃;

Reference yield:

tert-butyl 4-((2S,5R)-6-hydroxy-7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carboxamido)piperidine-1-carboxylate hydrate (1174020-64-4) → (2S,5R)-sulfuric acid mono{[(4-aminopiperidin-4-yl)carbonyl]-7-oxo-1,6-diazabicyclo[3.2.1]oct-6-yl}ester (1174018-99-5)

Guidance literature:

Multi-step reaction with 2 steps

1: sulfur trioxide pyridine complex; pyridine / 25 °C

2: trifluoroacetic acid / dichloromethane

With pyridine; sulfur trioxide pyridine complex; trifluoroacetic acid; In dichloromethane;

DOI:10.1016/j.bmcl.2013.12.101

upstream raw materials:

(2S,5R)-5-hydroxypiperidine-2-carboxylic acid

Downstream raw materials:

tert-butyl 4-[({(2S,5R)-7-oxo-6-[(phenoxycarbonothioyl)oxy]-1,6-diazabicyclo[3.2.1]oct-2-yl}carbonyl)amino]piperidine-1-carboxylate

(2S,5R)-sulfuric acid mono{[(4-aminopiperidin-4-yl)carbonyl]-7-oxo-1,6-diazabicyclo[3.2.1]oct-6-yl}ester

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