3-(2-Nitro-benzenesulfonyl)-11-(2,2,2-trifluoro-acetyl)-3,7,11-triaza-bicyclo[11.3.1]heptadeca-1⁽¹⁶⁾,13⁽¹⁷⁾,14-triene-7,15-dicarboxylic acid 7-allyl ester 15-methyl ester

Base Information

• Chemical Name: 3-(2-Nitro-benzenesulfonyl)-11-(2,2,2-trifluoro-acetyl)-3,7,11-triaza-bicyclo[11.3.1]heptadeca-1⁽¹⁶⁾,13⁽¹⁷⁾,14-triene-7,15-dicarboxylic acid 7-allyl ester 15-methyl ester
• CAS No.: 380235-21-2
• Molecular Formula: C₂₈H₃₁F₃N₄O₉S
• Molecular Weight: 656.637

Synonyms:3-(2-Nitro-benzenesulfonyl)-11-(2,2,2-trifluoro-acetyl)-3,7,11-triaza-bicyclo[11.3.1]heptadeca-1⁽¹⁶⁾,13⁽¹⁷⁾,14-triene-7,15-dicarboxylic acid 7-allyl ester 15-methyl ester

Chemical Property of 3-(2-Nitro-benzenesulfonyl)-11-(2,2,2-trifluoro-acetyl)-3,7,11-triaza-bicyclo[11.3.1]heptadeca-1⁽¹⁶⁾,13⁽¹⁷⁾,14-triene-7,15-dicarboxylic acid 7-allyl ester 15-methyl ester

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Technology Process of 3-(2-Nitro-benzenesulfonyl)-11-(2,2,2-trifluoro-acetyl)-3,7,11-triaza-bicyclo[11.3.1]heptadeca-1⁽¹⁶⁾,13⁽¹⁷⁾,14-triene-7,15-dicarboxylic acid 7-allyl ester 15-methyl ester

There total 8 articles about 3-(2-Nitro-benzenesulfonyl)-11-(2,2,2-trifluoro-acetyl)-3,7,11-triaza-bicyclo[11.3.1]heptadeca-1⁽¹⁶⁾,13⁽¹⁷⁾,14-triene-7,15-dicarboxylic acid 7-allyl ester 15-methyl 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: 51.0%

methyl 3,5-bis(bromomethyl)benzoate (29333-41-3) + allyl (3-(2-nitrophenylsulfonamido)propyl)(3-(2,2,2-trifluoroacetamido)propyl)carbamate (380235-20-1) → 3-(2-Nitro-benzenesulfonyl)-11-(2,2,2-trifluoro-acetyl)-3,7,11-triaza-bicyclo[11.3.1]heptadeca-1(16),13(17),14-triene-7,15-dicarboxylic acid 7-allyl ester 15-methyl ester (380235-21-2)

Guidance literature:

With caesium carbonate; In N,N-dimethyl-formamide; at 20 ℃;

DOI:10.1016/j.tet.2014.04.084

Reference yield: 47.0%

methyl 3,5-bis(bromomethyl)benzoate (29333-41-3) + allyl (3-(2-nitrophenylsulfonamido)propyl)(3-(2,2,2-trifluoroacetamido)propyl)carbamate (380235-20-1) → 3-(2-Nitro-benzenesulfonyl)-11-(2,2,2-trifluoro-acetyl)-3,7,11-triaza-bicyclo[11.3.1]heptadeca-1(16),13(17),14-triene-7,15-dicarboxylic acid 7-allyl ester 15-methyl ester (380235-21-2) + 11,27-Bis-(2-nitro-benzenesulfonyl)-3,19-bis-(2,2,2-trifluoro-acetyl)-3,7,11,19,23,27-hexaaza-tricyclo[27.3.1.113,17]tetratriaconta-1(33),13,15,17(34),29,31-hexaene-7,15,23,31-tetracarboxylic acid 7,23-diallyl ester 15,31-dimethyl ester

Guidance literature:

With tetrabutylammomium bromide; caesium carbonate; In acetonitrile; Heating;

DOI:10.1021/ol0101741

Reference yield:

2-Nitrobenzenesulfonyl chloride (1694-92-4) → 3-(2-Nitro-benzenesulfonyl)-11-(2,2,2-trifluoro-acetyl)-3,7,11-triaza-bicyclo[11.3.1]heptadeca-1(16),13(17),14-triene-7,15-dicarboxylic acid 7-allyl ester 15-methyl ester (380235-21-2)

Guidance literature:

Multi-step reaction with 4 steps

1: CH₂Cl₂ / 0.75 h / 0 - 20 °C

2: H₂O / acetonitrile / 16 h / Heating

3: 85 percent / NaHCO₃ / H₂O; dioxane / 4 h / 20 °C

4: 46.7 percent / Cs₂CO₃; Bu₄NBr / acetonitrile / 0.58 h / Heating

With tetrabutylammomium bromide; water; sodium hydrogencarbonate; caesium carbonate; In 1,4-dioxane; dichloromethane; water; acetonitrile;

DOI:10.1021/ol0101741

upstream raw materials:

methyl 3,5-bis(bromomethyl)benzoate

allyl (3-(2-nitrophenylsulfonamido)propyl)(3-(2,2,2-trifluoroacetamido)propyl)carbamate

bis(3-aminopropyl)amine

2-Nitrobenzenesulfonyl chloride

Downstream raw materials:

11-(2-nitro-benzenesulfonyl)-3,7,11-triaza-bicyclo[11.3.1]heptadeca-1⁽¹⁷⁾,13,15-triene-3,7,15-tricarboxylic acid 7-allyl ester 3-(9H-fluoren-9-ylmethyl) ester

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