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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Chemical Name:2-oxo-9-thia-3,12-diaza-tricyclo[8.2.1.0(3,7)]tridecane-12-benzyloxycarbonyl-4-carboxylic acid tert-butyl ester
CAS No.:376585-22-7
Molecular Formula:C₂₃H₃₀N₂O₅S
Molecular Weight:446.568
Hs Code.:

Synonyms: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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Chemical Property of 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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Technology Process of 2-oxo-9-thia-3,12-diaza-tricyclo[8.2.1.0(3,7)]tridecane-12-benzyloxycarbonyl-4-carboxylic acid tert-butyl ester

There total 11 articles about 2-oxo-9-thia-3,12-diaza-tricyclo[8.2.1.0(3,7)]tridecane-12-benzyloxycarbonyl-4-carboxylic acid tert-butyl 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: 94.0%

: 507-19-7
t-butyl bromide

: 727727-10-8
(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

: 376585-22-7
2-oxo-9-thia-3,12-diaza-tricyclo[8.2.1.0(3,7)]tridecane-12-benzyloxycarbonyl-4-carboxylic acid tert-butyl ester

Guidance literature:: With N-benzyl-N,N,N-triethylammonium chloride; potassium carbonate; In N,N-dimethyl acetamide; at 50 ℃; for 24h;
DOI:10.1021/ja010812a

Reference yield:

: 40216-83-9
L-4-hydroxyproline methyl ester hydrochloride

: 376585-22-7
2-oxo-9-thia-3,12-diaza-tricyclo[8.2.1.0(3,7)]tridecane-12-benzyloxycarbonyl-4-carboxylic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 9 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

9.1: 94 percent / benzyltriethylammonium chloride; K₂CO₃ / N,N-dimethyl-acetamide / 24 h / 50 °C

With sodium hydroxide; potassium methanolate; N-benzyl-N,N,N-triethylammonium chloride; sodium hydrogencarbonate; potassium carbonate; N-ethyl-N,N-diisopropylamine; 1,1'-carbonyldiimidazole; trifluoroacetic acid; In 1,4-dioxane; pyridine; methanol; dichloromethane; N,N-dimethyl acetamide; water; toluene; acetonitrile;
DOI:10.1021/ja010812a

Reference yield:

: 376585-20-5
5-[1-benzyloxycarbonyl-4-(toluene-4-sulfonyloxy)-pyrrolidine-2-carbonyl]-mercaptomethyl-pyrrolidine-2-carboxylic acid methyl ester

: 376585-22-7
2-oxo-9-thia-3,12-diaza-tricyclo[8.2.1.0(3,7)]tridecane-12-benzyloxycarbonyl-4-carboxylic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 3 steps

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

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

3: 94 percent / benzyltriethylammonium chloride; K₂CO₃ / N,N-dimethyl-acetamide / 24 h / 50 °C

With sodium hydroxide; potassium methanolate; N-benzyl-N,N,N-triethylammonium chloride; potassium carbonate; In methanol; N,N-dimethyl acetamide; acetonitrile;
DOI:10.1021/ja010812a