5-Methoxy-3,4-dioxo-cyclohexa-1,5-dienecarboxylic acid (S)-2-carboxy-2-(5-dimethylamino-naphthalene-1-sulfonylamino)-ethyl ester

Base Information

Chemical Name:5-Methoxy-3,4-dioxo-cyclohexa-1,5-dienecarboxylic acid (S)-2-carboxy-2-(5-dimethylamino-naphthalene-1-sulfonylamino)-ethyl ester
CAS No.:246047-89-2
Molecular Formula:C₂₃H₂₂N₂O₉S
Molecular Weight:502.502
Hs Code.:

Synonyms:5-Methoxy-3,4-dioxo-cyclohexa-1,5-dienecarboxylic acid (S)-2-carboxy-2-(5-dimethylamino-naphthalene-1-sulfonylamino)-ethyl ester

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Chemical Property of 5-Methoxy-3,4-dioxo-cyclohexa-1,5-dienecarboxylic acid (S)-2-carboxy-2-(5-dimethylamino-naphthalene-1-sulfonylamino)-ethyl ester

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Technology Process of 5-Methoxy-3,4-dioxo-cyclohexa-1,5-dienecarboxylic acid (S)-2-carboxy-2-(5-dimethylamino-naphthalene-1-sulfonylamino)-ethyl ester

There total 4 articles about 5-Methoxy-3,4-dioxo-cyclohexa-1,5-dienecarboxylic acid (S)-2-carboxy-2-(5-dimethylamino-naphthalene-1-sulfonylamino)-ethyl 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: 44.0%

: 246048-06-6
(S)-2-(5-(dimethylamino)naphthalene-1-sulfonamidyl)-3-((3,4-dihydroxy-5-methoxybenzoyl)oxy)propionic acid

: 246047-89-2
5-Methoxy-3,4-dioxo-cyclohexa-1,5-dienecarboxylic acid (S)-2-carboxy-2-(5-dimethylamino-naphthalene-1-sulfonylamino)-ethyl ester

Guidance literature:: With o-tetrachloroquinone; In tetrahydrofuran; diethyl ether; at -42 - -20 ℃; for 12.5h;
DOI:10.1021/jo982477n

Reference yield:

: 605-65-2
5-(dimethylamino)naphth-1-ylsulfonyl chloride

: 246047-89-2
5-Methoxy-3,4-dioxo-cyclohexa-1,5-dienecarboxylic acid (S)-2-carboxy-2-(5-dimethylamino-naphthalene-1-sulfonylamino)-ethyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: 88 percent / NaHCO₃ / acetone; H₂O / 14 h

2: 70 percent / DMAP; DIC / CH₂Cl₂ / 20 °C

3: 98 percent / H₂ / Pd/C / tetrahydrofuran / 14 h / 20 °C / 760 Torr

4: 44 percent / orthochloranil / tetrahydrofuran; diethyl ether / 12.5 h / -42 - -20 °C

With dmap; o-tetrachloroquinone; hydrogen; sodium hydrogencarbonate; dacarbazine; palladium on activated charcoal; In tetrahydrofuran; diethyl ether; dichloromethane; water; acetone; 1: Substitution / 2: Esterification / 3: Catalytic hydrogenation / 4: Oxidation;
DOI:10.1021/jo982477n

Reference yield:

: 246048-04-4
benzyl (S)-2-(5-(dimethylamino)naphthalene-1-sulfonamidyl)-3-hydroxypropionate

: 246047-89-2
5-Methoxy-3,4-dioxo-cyclohexa-1,5-dienecarboxylic acid (S)-2-carboxy-2-(5-dimethylamino-naphthalene-1-sulfonylamino)-ethyl ester

Guidance literature:: Multi-step reaction with 3 steps

1: 70 percent / DMAP; DIC / CH₂Cl₂ / 20 °C

2: 98 percent / H₂ / Pd/C / tetrahydrofuran / 14 h / 20 °C / 760 Torr

3: 44 percent / orthochloranil / tetrahydrofuran; diethyl ether / 12.5 h / -42 - -20 °C

With dmap; o-tetrachloroquinone; hydrogen; dacarbazine; palladium on activated charcoal; In tetrahydrofuran; diethyl ether; dichloromethane; 1: Esterification / 2: Catalytic hydrogenation / 3: Oxidation;
DOI:10.1021/jo982477n