1-N-(p-Methoxyphenyl)-(3S,4R)-3-[1(R)-hydroxyethyl]-4-phenylsulfonylazetidin-2-one

Base Information

• Chemical Name: 1-N-(p-Methoxyphenyl)-(3S,4R)-3-[1(R)-hydroxyethyl]-4-phenylsulfonylazetidin-2-one
• CAS No.: 84939-40-2
• Molecular Formula: C₁₈H₁₉NO₅S
• Molecular Weight: 361.419

Synonyms:1-N-(p-Methoxyphenyl)-(3S,4R)-3-[1(R)-hydroxyethyl]-4-phenylsulfonylazetidin-2-one

Chemical Property of 1-N-(p-Methoxyphenyl)-(3S,4R)-3-[1(R)-hydroxyethyl]-4-phenylsulfonylazetidin-2-one

Chemical Property:

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Technology Process of 1-N-(p-Methoxyphenyl)-(3S,4R)-3-[1(R)-hydroxyethyl]-4-phenylsulfonylazetidin-2-one

There total 11 articles about 1-N-(p-Methoxyphenyl)-(3S,4R)-3-[1(R)-hydroxyethyl]-4-phenylsulfonylazetidin-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: 82.0%

(2R,3R)-3-Methyl-oxirane-2-carboxylic acid benzenesulfonylmethyl-(4-methoxy-phenyl)-amide (84939-22-0) → 1-N-(p-Methoxyphenyl)-(3S,4R)-3-[1(R)-hydroxyethyl]-4-phenylsulfonylazetidin-2-one (84939-40-2)

Guidance literature:

With n-butyllithium; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; at -50 ℃; for 0.5h;

DOI:10.1016/S0040-4039(00)81597-X

Reference yield: 55.0%

→ 1-N-(p-Methoxyphenyl)-(3S,4R)-3-[1(R)-hydroxyethyl]-4-phenylsulfonylazetidin-2-one (84939-40-2)

Guidance literature:

Reference yield:

2R,3R-2,3-epoxybutyric acid-p-methoxyphenylamide (84939-32-2) → 1-N-(p-Methoxyphenyl)-(3S,4R)-3-[1(R)-hydroxyethyl]-4-phenylsulfonylazetidin-2-one (84939-40-2)

Guidance literature:

Multi-step reaction with 4 steps

1: 87 percent / 50percent aq. NaOH / benzyltriethylammonium iodide / CH₂Cl₂ / 1 h / Ambient temperature

2: m-chloroperbenzoic acid

3: 17 percent / N-butyllithium / tetrahydrofuran; hexamethylphosphoric acid triamide / 0.5 h / -50 °C

4: m-chloroperbenzoic acid

With sodium hydroxide; n-butyllithium; 3-chloro-benzenecarboperoxoic acid; triethylbenzylammonium iodide; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; dichloromethane;

DOI:10.1016/S0040-4039(00)81597-X

upstream raw materials:

(3S,4R)-4-Benzenesulfinyl-3-((R)-1-hydroxy-ethyl)-1-(4-methoxy-phenyl)-azetidin-2-one

(2R,3R)-3-Methyl-oxirane-2-carboxylic acid benzenesulfonylmethyl-(4-methoxy-phenyl)-amide

(3S,4R)-3-((R)-1-Hydroxy-ethyl)-1-(4-methoxy-phenyl)-4-phenylsulfanyl-azetidin-2-one

phenylthiomethyl chloride

Downstream raw materials:

3S-<1R-(methoxymethoxy)-ethyl>-4R-(phenylsulfonyl)-azetidin-2-one

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