cis-(4R)-t-butylthio-1-ethoxycarbonylmethyl-(3R)-phenylacetamidoazetidin-2-one

Base Information

• Chemical Name: cis-(4R)-t-butylthio-1-ethoxycarbonylmethyl-(3R)-phenylacetamidoazetidin-2-one
• CAS No.: 1424272-92-3
• Molecular Formula: C₁₉H₂₆N₂O₄S
• Molecular Weight: 378.492
• Mol file: 1424272-92-3.mol

Synonyms:cis-(4R)-t-butylthio-1-ethoxycarbonylmethyl-(3R)-phenylacetamidoazetidin-2-one

Chemical Property of cis-(4R)-t-butylthio-1-ethoxycarbonylmethyl-(3R)-phenylacetamidoazetidin-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of cis-(4R)-t-butylthio-1-ethoxycarbonylmethyl-(3R)-phenylacetamidoazetidin-2-one

There total 5 articles about cis-(4R)-t-butylthio-1-ethoxycarbonylmethyl-(3R)-phenylacetamidoazetidin-2-one 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: 74.0%

ethyl bromoacetate (105-36-2) + cis-(4R)-t-butylthio-(3R)-phenylacetamidoazetidin-2-one (74213-37-9) → cis-(4R)-t-butylthio-1-ethoxycarbonylmethyl-(3R)-phenylacetamidoazetidin-2-one (1424272-92-3)

Guidance literature:

With potassium carbonate; In N,N-dimethyl-formamide; at 60 ℃; for 10h;

DOI:10.5012/bkcs.2013.34.1.121

Reference yield:

benzyl (2S,5R,6R)-3,3-dimethyl-7-oxo-6-(2-phenylacetamido)-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate (1254-56-4) → cis-(4R)-t-butylthio-1-ethoxycarbonylmethyl-(3R)-phenylacetamidoazetidin-2-one (1424272-92-3)

Guidance literature:

Multi-step reaction with 4 steps

1.1: mercury(II) diacetate / acetic acid / 0.5 h / 80 °C

1.2: 2 h / 80 - 85 °C

2.1: ozone / dichloromethane; methanol / 2 h / -78 °C

2.2: 20 °C

3.1: water; tetrahydrofuran / 4 h / 0 - 20 °C

4.1: potassium carbonate / N,N-dimethyl-formamide / 10 h / 60 °C

With mercury(II) diacetate; potassium carbonate; ozone; In tetrahydrofuran; methanol; dichloromethane; water; acetic acid; N,N-dimethyl-formamide;

DOI:10.5012/bkcs.2013.34.1.121

Reference yield:

trans-(4S)-acetoxy-1-(1-benzyloxycarbonyl-2-methylpropenyl)-(3S)-phenylacetamidoazetidin-2-one (106847-31-8) → cis-(4R)-t-butylthio-1-ethoxycarbonylmethyl-(3R)-phenylacetamidoazetidin-2-one (1424272-92-3)

Guidance literature:

Multi-step reaction with 3 steps

1.1: ozone / dichloromethane; methanol / 2 h / -78 °C

1.2: 20 °C

2.1: water; tetrahydrofuran / 4 h / 0 - 20 °C

3.1: potassium carbonate / N,N-dimethyl-formamide / 10 h / 60 °C

With potassium carbonate; ozone; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.5012/bkcs.2013.34.1.121

upstream raw materials:

Penicillin G potassium

benzyl (2S,5R,6R)-3,3-dimethyl-7-oxo-6-(2-phenylacetamido)-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate

trans-(4S)-acetoxy-1-(1-benzyloxycarbonyl-2-methylpropenyl)-(3S)-phenylacetamidoazetidin-2-one

(2S-trans)-N-<2-(acetyloxy)-4-oxo-3-azetidinyl>benzeneacetamide

Downstream raw materials:

C₁₇H₂₁N₂O₄S^(1-)*K⁽¹⁺⁾