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

Base Information

• Chemical Name: trans-(4S)-acetoxy-1-(1-benzyloxycarbonyl-2-methylpropenyl)-(3S)-phenylacetamidoazetidin-2-one
• CAS No.: 106847-31-8
• Molecular Formula: C₂₅H₂₆N₂O₆
• Molecular Weight: 450.491
• Mol file: 106847-31-8.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 2 articles about trans-(4S)-acetoxy-1-(1-benzyloxycarbonyl-2-methylpropenyl)-(3S)-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: 60.0%

acetic anhydride (108-24-7) + 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) → trans-(4S)-acetoxy-1-(1-benzyloxycarbonyl-2-methylpropenyl)-(3S)-phenylacetamidoazetidin-2-one (106847-31-8)

Guidance literature:

acetic anhydride; With mercury(II) diacetate; In acetic acid; at 80 ℃; for 0.5h;

benzyl (2S,5R,6R)-3,3-dimethyl-7-oxo-6-(2-phenylacetamido)-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate; In acetic anhydride; acetic acid; at 80 - 85 ℃; for 2h;

DOI:10.5012/bkcs.2013.34.1.121

Reference yield:

Penicillin G potassium (113-98-4) + benzyl bromide (100-39-0) → trans-(4S)-acetoxy-1-(1-benzyloxycarbonyl-2-methylpropenyl)-(3S)-phenylacetamidoazetidin-2-one (106847-31-8)

Guidance literature:

Multi-step reaction with 2 steps

1.1: N,N-dimethyl-formamide / 2 h / 20 °C

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

2.2: 2 h / 80 - 85 °C

With mercury(II) diacetate; In acetic acid; N,N-dimethyl-formamide;

DOI:10.5012/bkcs.2013.34.1.121

Reference yield: 80.0%

trans-(4S)-acetoxy-1-(1-benzyloxycarbonyl-2-methylpropenyl)-(3S)-phenylacetamidoazetidin-2-one (106847-31-8) → (2S-trans)-N-<2-(acetyloxy)-4-oxo-3-azetidinyl>benzeneacetamide (85027-68-5)

Guidance literature:

trans-(4S)-acetoxy-1-(1-benzyloxycarbonyl-2-methylpropenyl)-(3S)-phenylacetamidoazetidin-2-one; With ozone; In methanol; dichloromethane; at -78 ℃; for 2h;

With dimethylsulfide; In methanol; dichloromethane; at 20 ℃;

DOI:10.5012/bkcs.2013.34.1.121

upstream raw materials:

Penicillin G potassium

benzyl bromide

acetic anhydride

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

Downstream raw materials:

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

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

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

C₁₇H₂₁N₂O₄S^(1-)*K⁽¹⁺⁾