(1S,4S,7S,10S)-2-Oxo-9-thia-3,12-diaza-tricyclo[8.2.1.0^3,7]tridecane-4,12-dicarboxylic acid 12-benzyl ester

Base Information

• Chemical Name: (1S,4S,7S,10S)-2-Oxo-9-thia-3,12-diaza-tricyclo[8.2.1.0^3,7]tridecane-4,12-dicarboxylic acid 12-benzyl ester
• CAS No.: 727727-10-8
• Molecular Formula: C₁₉H₂₂N₂O₅S
• Molecular Weight: 390.46

Synonyms:(1S,4S,7S,10S)-2-Oxo-9-thia-3,12-diaza-tricyclo[8.2.1.0^3,7]tridecane-4,12-dicarboxylic acid 12-benzyl ester

Chemical Property of (1S,4S,7S,10S)-2-Oxo-9-thia-3,12-diaza-tricyclo[8.2.1.0^3,7]tridecane-4,12-dicarboxylic acid 12-benzyl ester

Chemical Property:

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Technology Process of (1S,4S,7S,10S)-2-Oxo-9-thia-3,12-diaza-tricyclo[8.2.1.0^3,7]tridecane-4,12-dicarboxylic acid 12-benzyl ester

There total 10 articles about (1S,4S,7S,10S)-2-Oxo-9-thia-3,12-diaza-tricyclo[8.2.1.0^3,7]tridecane-4,12-dicarboxylic acid 12-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: 68.0%

2-oxo-9-thia-3,12-diaza-tricyclo[8.2.1.0(3,7)]tridecane-12-benzyloxycarbonyl-4-carboxylic acid methyl ester (376585-21-6) → (1S,4S,7S,10S)-2-Oxo-9-thia-3,12-diaza-tricyclo[8.2.1.03,7]tridecane-4,12-dicarboxylic acid 12-benzyl ester (727727-10-8)

Guidance literature:

With sodium hydroxide; In methanol; at 20 ℃; for 20h;

DOI:10.1021/ja010812a

Reference yield:

L-4-hydroxyproline methyl ester hydrochloride (40216-83-9) → (1S,4S,7S,10S)-2-Oxo-9-thia-3,12-diaza-tricyclo[8.2.1.03,7]tridecane-4,12-dicarboxylic acid 12-benzyl ester (727727-10-8)

Guidance literature:

Multi-step reaction with 8 steps

1.1: 100 percent / sodium bicarbonate / H₂O; dioxane / 23 h / 0 - 20 °C

2.1: 63 percent / pyridine / 22 h / 4 °C

3.1: 93 percent / aq. NaOH / methanol / 15 h / 0 - 20 °C

4.1: 1,1-carbonyldiimidazole / acetonitrile / 1 h / 0 °C

4.2: 100 percent / acetonitrile / 16 h / 0 - 20 °C

5.1: trifluoroacetic acid / CH₂Cl₂ / 2 h / 0 °C

6.1: 7.99 g / N,N-diisopropylethylamine / toluene / 3 h / 60 °C

7.1: 93 percent / KOMe / acetonitrile; methanol / 1 h / Heating

8.1: 68 percent / aq. NaOH / methanol / 20 h / 20 °C

With sodium hydroxide; potassium methanolate; sodium hydrogencarbonate; N-ethyl-N,N-diisopropylamine; 1,1'-carbonyldiimidazole; trifluoroacetic acid; In 1,4-dioxane; pyridine; methanol; dichloromethane; water; toluene; acetonitrile;

DOI:10.1021/ja010812a

Reference yield:

5-[1-benzyloxycarbonyl-4-(toluene-4-sulfonyloxy)-pyrrolidine-2-carbonyl]-mercaptomethyl-pyrrolidine-2-carboxylic acid methyl ester (376585-20-5) → (1S,4S,7S,10S)-2-Oxo-9-thia-3,12-diaza-tricyclo[8.2.1.03,7]tridecane-4,12-dicarboxylic acid 12-benzyl ester (727727-10-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 93 percent / KOMe / acetonitrile; methanol / 1 h / Heating

2: 68 percent / aq. NaOH / methanol / 20 h / 20 °C

With sodium hydroxide; potassium methanolate; In methanol; acetonitrile;

DOI:10.1021/ja010812a

upstream raw materials:

2-oxo-9-thia-3,12-diaza-tricyclo[8.2.1.0(3,7)]tridecane-12-benzyloxycarbonyl-4-carboxylic acid methyl ester

5-[1-benzyloxycarbonyl-4-(toluene-4-sulfonyloxy)-pyrrolidine-2-carbonyl]-mercaptomethyl-pyrrolidine-2-carboxylic acid methyl ester

5-[1-benzyloxycarbonyl-4-(toluene-4-sulfonyloxy)-pyrrolidine-2-carbonylsulfanylmethyl]-1-tert-butyloxycarbonyl-pyrrolidine-2-carboxylic acid methyl ester

L-4-hydroxyproline methyl ester hydrochloride

Downstream raw materials:

2-oxo-9-thia-3,12-diaza-tricyclo[8.2.1.0(3,7)]tridecane-12-benzyloxycarbonyl-4-carboxylic acid tert-butyl ester

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