(1R,2S)-2-(4-tolylsulfamoyl)-2-(methoxycarbonyl)-1-methylethyl acetoacetate

Base Information

• Chemical Name: (1R,2S)-2-(4-tolylsulfamoyl)-2-(methoxycarbonyl)-1-methylethyl acetoacetate
• CAS No.: 128107-92-6
• Molecular Formula: C₁₆H₂₁NO₇S
• Molecular Weight: 371.411

Synonyms:(1R,2S)-2-(4-tolylsulfamoyl)-2-(methoxycarbonyl)-1-methylethyl acetoacetate

Chemical Property of (1R,2S)-2-(4-tolylsulfamoyl)-2-(methoxycarbonyl)-1-methylethyl acetoacetate

Chemical Property:

Purity/Quality:

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Technology Process of (1R,2S)-2-(4-tolylsulfamoyl)-2-(methoxycarbonyl)-1-methylethyl acetoacetate

There total 2 articles about (1R,2S)-2-(4-tolylsulfamoyl)-2-(methoxycarbonyl)-1-methylethyl acetoacetate 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: 98.0%

4-methyleneoxetan-2-one (674-82-8,2130-41-8) + (2S,3R)-methyl-N-(4-methylphenylsulfonyl)-3-hydroxy-2-aminobutanoate (43188-53-0) → (1R,2S)-2-(4-tolylsulfamoyl)-2-(methoxycarbonyl)-1-methylethyl acetoacetate (128107-92-6)

Guidance literature:

With dmap; In tetrahydrofuran; at 25 ℃; for 2h;

DOI:10.1021/jm00015a007

Reference yield:

p-toluenesulfonyl chloride (98-59-9) → (1R,2S)-2-(4-tolylsulfamoyl)-2-(methoxycarbonyl)-1-methylethyl acetoacetate (128107-92-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 72 percent / K₂CO₃ / ethyl acetate; H₂O / 20 h / 5 - 25 °C

2: 98 percent / 4-(dimethylamino)pyridine / tetrahydrofuran / 2 h / 25 °C

With dmap; potassium carbonate; In tetrahydrofuran; water; ethyl acetate;

DOI:10.1021/jm00015a007

Reference yield: 52.5%

(1R,2S)-2-(4-tolylsulfamoyl)-2-(methoxycarbonyl)-1-methylethyl acetoacetate (128107-92-6) → (1R,2S)-2-(4-tolylsulfamoyl)-2-(methoxycarbonyl)-1-methylethyl β-aminocrotonate (166733-04-6)

Guidance literature:

With ammonia; toluene-4-sulfonic acid; In toluene; at 130 ℃; for 4h;

DOI:10.1021/jm00015a007

upstream raw materials:

4-methyleneoxetan-2-one

(2S,3R)-methyl-N-(4-methylphenylsulfonyl)-3-hydroxy-2-aminobutanoate

p-toluenesulfonyl chloride

Downstream raw materials:

(1R,2S)-2-(4-tolylsulfamoyl)-2-(methoxycarbonyl)-1-methylethyl β-aminocrotonate

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