18-((4-iodophenyl)sulfonyl)-16-methylidene-2-oxo-12-oxa-3,18-diazatricyclo[18.3.1.0^6,11]tetraeicosa-1⁽²⁴⁾,6,8,10,14,20,22-heptaene-4-carboxylic acid

Base Information

• Chemical Name: 18-((4-iodophenyl)sulfonyl)-16-methylidene-2-oxo-12-oxa-3,18-diazatricyclo[18.3.1.0^6,11]tetraeicosa-1⁽²⁴⁾,6,8,10,14,20,22-heptaene-4-carboxylic acid
• CAS No.: 669062-28-6
• Molecular Formula: C₂₉H₂₇IN₂O₆S
• Molecular Weight: 658.514

Synonyms:18-((4-iodophenyl)sulfonyl)-16-methylidene-2-oxo-12-oxa-3,18-diazatricyclo[18.3.1.0^6,11]tetraeicosa-1⁽²⁴⁾,6,8,10,14,20,22-heptaene-4-carboxylic acid

Chemical Property of 18-((4-iodophenyl)sulfonyl)-16-methylidene-2-oxo-12-oxa-3,18-diazatricyclo[18.3.1.0^6,11]tetraeicosa-1⁽²⁴⁾,6,8,10,14,20,22-heptaene-4-carboxylic acid

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Technology Process of 18-((4-iodophenyl)sulfonyl)-16-methylidene-2-oxo-12-oxa-3,18-diazatricyclo[18.3.1.0^6,11]tetraeicosa-1⁽²⁴⁾,6,8,10,14,20,22-heptaene-4-carboxylic acid

There total 11 articles about 18-((4-iodophenyl)sulfonyl)-16-methylidene-2-oxo-12-oxa-3,18-diazatricyclo[18.3.1.0^6,11]tetraeicosa-1⁽²⁴⁾,6,8,10,14,20,22-heptaene-4-carboxylic acid 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: 87.0%

methyl 18-((4-iodophenyl)sulfonyl)-16-methylidene-2-oxo-12-oxa-3,18-diazatricyclo[18.3.1.06,11]tetraeicosa-1(24),6,8,10,14,20,22-heptaene-4-carboxylate (669062-08-2) → 18-((4-iodophenyl)sulfonyl)-16-methylidene-2-oxo-12-oxa-3,18-diazatricyclo[18.3.1.06,11]tetraeicosa-1(24),6,8,10,14,20,22-heptaene-4-carboxylic acid (669062-28-6)

Guidance literature:

With lithium hydroxide; In tetrahydrofuran; at 20 ℃; for 4h;

DOI:10.1021/jo0352629

Reference yield:

3-(Chloromethyl)benzoyl chloride (63024-77-1) → 18-((4-iodophenyl)sulfonyl)-16-methylidene-2-oxo-12-oxa-3,18-diazatricyclo[18.3.1.06,11]tetraeicosa-1(24),6,8,10,14,20,22-heptaene-4-carboxylic acid (669062-28-6)

Guidance literature:

Multi-step reaction with 4 steps

1: 0.536 g / Et₃N / CH₂Cl₂ / 4 h / 0 °C

2: 87 percent / NaH / dimethylformamide

3: 56 percent / PCy₃Cl₂((Mes)2C₃H₅N₂)Ru(=CHPh) / 4 h / 20 °C

4: 87 percent / aq. LiOH / tetrahydrofuran / 4 h / 20 °C

With tri(cycloxexyl)phosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidene][benzylidene]ruthenium(IV) dichloride; lithium hydroxide; sodium hydride; triethylamine; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jo0352629

Reference yield:

p-Iodobenzenesulfonyl chloride (98-61-3) → 18-((4-iodophenyl)sulfonyl)-16-methylidene-2-oxo-12-oxa-3,18-diazatricyclo[18.3.1.06,11]tetraeicosa-1(24),6,8,10,14,20,22-heptaene-4-carboxylic acid (669062-28-6)

Guidance literature:

Multi-step reaction with 4 steps

1: 45 percent / Et₃N / CH₂Cl₂ / 20 h / 0 °C

2: 87 percent / NaH / dimethylformamide

3: 56 percent / PCy₃Cl₂((Mes)2C₃H₅N₂)Ru(=CHPh) / 4 h / 20 °C

4: 87 percent / aq. LiOH / tetrahydrofuran / 4 h / 20 °C

With tri(cycloxexyl)phosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidene][benzylidene]ruthenium(IV) dichloride; lithium hydroxide; sodium hydride; triethylamine; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jo0352629

upstream raw materials:

methyl 18-((4-iodophenyl)sulfonyl)-16-methylidene-2-oxo-12-oxa-3,18-diazatricyclo[18.3.1.0^6,11]tetraeicosa-1⁽²⁴⁾,6,8,10,14,20,22-heptaene-4-carboxylate

3-(Chloromethyl)benzoyl chloride

p-Iodobenzenesulfonyl chloride

2-hydroxy-phenylalanine

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