*-trans)>-4,5-dihydro-4-hydroxy-1-methyl-3-oxo-3H-1λ⁴-isothiazole-4-acetic acid benzyl ester

Base Information

• Chemical Name: *-trans)>-4,5-dihydro-4-hydroxy-1-methyl-3-oxo-3H-1λ⁴-isothiazole-4-acetic acid benzyl ester
• CAS No.: 144373-39-7
• Molecular Formula: C₁₃H₁₅NO₅S
• Molecular Weight: 297.332

Synonyms:*-trans)>-4,5-dihydro-4-hydroxy-1-methyl-3-oxo-3H-1λ⁴-isothiazole-4-acetic acid benzyl ester

Chemical Property of *-trans)>-4,5-dihydro-4-hydroxy-1-methyl-3-oxo-3H-1λ⁴-isothiazole-4-acetic acid benzyl ester

Chemical Property:

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Technology Process of *-trans)>-4,5-dihydro-4-hydroxy-1-methyl-3-oxo-3H-1λ⁴-isothiazole-4-acetic acid benzyl ester

There total 5 articles about *-trans)>-4,5-dihydro-4-hydroxy-1-methyl-3-oxo-3H-1λ⁴-isothiazole-4-acetic acid benzyl ester 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: 100.0%

*,R*)>-2-hydroxy-2-<(S-methylsulfonimidoyl)methyl>butanedioic acid dibenzyl ester (144373-38-6) → *-trans)>-4,5-dihydro-4-hydroxy-1-methyl-3-oxo-3H-1λ4-isothiazole-4-acetic acid benzyl ester (144373-39-7)

Guidance literature:

In ethanol; water; Heating;

DOI:10.1021/jm00104a014

Reference yield:

4-(methylthio)-3-oxobutanoic acid methyl ester (64127-51-1) → *-trans)>-4,5-dihydro-4-hydroxy-1-methyl-3-oxo-3H-1λ4-isothiazole-4-acetic acid benzyl ester (144373-39-7)

Guidance literature:

Multi-step reaction with 5 steps

1: 1.) conc. HCl, 2.) conc. HCl, 3.) 3 N aq. HCl

2: 61 percent / K₂CO₃ / dimethylformamide / 18 h / 60 °C

3: 31 percent / O₃, Sudan III / CH₂Cl₂ / -78 °C

4: 49 percent / O-(mesitylsulfonyl)hydroxylamine / CH₂Cl₂ / 18 h / 25 °C

5: 100 percent / ethanol; H₂O / Heating

With hydrogenchloride; oil scarlet; mesitylenesulfonylhydroxylamine; potassium carbonate; ozone; In ethanol; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1021/jm00104a014

Reference yield:

2-hydroxy-2-<(methylthio)methyl>butanedioic acid (144373-33-1) → *-trans)>-4,5-dihydro-4-hydroxy-1-methyl-3-oxo-3H-1λ4-isothiazole-4-acetic acid benzyl ester (144373-39-7)

Guidance literature:

Multi-step reaction with 4 steps

1: 61 percent / K₂CO₃ / dimethylformamide / 18 h / 60 °C

2: 31 percent / O₃, Sudan III / CH₂Cl₂ / -78 °C

3: 49 percent / O-(mesitylsulfonyl)hydroxylamine / CH₂Cl₂ / 18 h / 25 °C

4: 100 percent / ethanol; H₂O / Heating

With oil scarlet; mesitylenesulfonylhydroxylamine; potassium carbonate; ozone; In ethanol; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1021/jm00104a014

upstream raw materials:

*,R^*)>-2-hydroxy-2-<(S-methylsulfonimidoyl)methyl>butanedioic acid dibenzyl ester

4-(methylthio)-3-oxobutanoic acid methyl ester

2-hydroxy-2-<(methylthio)methyl>butanedioic acid

2-hydroxy-2-<(methylthio)methyl>butanedioic acid dibenzyl ester

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