methyl 2-({[2-({2-[(2S)-(N-tert-butoxycarbonyl)pyrrolidin-2-yl]ethyl}amino)phenyl]sulfonyl}amino)-5,6,7,8-tetrahydro-1-naphthalenecarboxylate

Base Information

• Chemical Name: methyl 2-({[2-({2-[(2S)-(N-tert-butoxycarbonyl)pyrrolidin-2-yl]ethyl}amino)phenyl]sulfonyl}amino)-5,6,7,8-tetrahydro-1-naphthalenecarboxylate
• CAS No.: 904680-11-1
• Molecular Formula: C₂₉H₃₉N₃O₆S
• Molecular Weight: 557.711

Synonyms:methyl 2-({[2-({2-[(2S)-(N-tert-butoxycarbonyl)pyrrolidin-2-yl]ethyl}amino)phenyl]sulfonyl}amino)-5,6,7,8-tetrahydro-1-naphthalenecarboxylate

Chemical Property of methyl 2-({[2-({2-[(2S)-(N-tert-butoxycarbonyl)pyrrolidin-2-yl]ethyl}amino)phenyl]sulfonyl}amino)-5,6,7,8-tetrahydro-1-naphthalenecarboxylate

Chemical Property:

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Technology Process of methyl 2-({[2-({2-[(2S)-(N-tert-butoxycarbonyl)pyrrolidin-2-yl]ethyl}amino)phenyl]sulfonyl}amino)-5,6,7,8-tetrahydro-1-naphthalenecarboxylate

There total 8 articles about methyl 2-({[2-({2-[(2S)-(N-tert-butoxycarbonyl)pyrrolidin-2-yl]ethyl}amino)phenyl]sulfonyl}amino)-5,6,7,8-tetrahydro-1-naphthalenecarboxylate 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:

2-trifluoromethanesulfonyloxy-5,6,7,8-tetrahydronaphthalene-1-carboxylic acid methyl ester (846540-87-2) → methyl 2-({[2-({2-[(2S)-(N-tert-butoxycarbonyl)pyrrolidin-2-yl]ethyl}amino)phenyl]sulfonyl}amino)-5,6,7,8-tetrahydro-1-naphthalenecarboxylate (904680-11-1)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 54.06 g / Cs₂CO₃; Pd(OAc)2; 4,5-bis-diphenylphosphanyl-9,9-dimethyl-9H-xanthene / dioxane / 4 h / 100 °C

2.1: 100 percent / aq. HCl / tetrahydrofuran / 1 h / 20 °C

3.1: pyridine / 20 °C

4.1: 1.8750 g / H₂ / Raney nickel / methanol; ethyl acetate / 2 h / 3102.89 Torr

5.1: Dess-Martin periodinane / N,N-dimethyl-acetamide; CH₂Cl₂ / 0.25 h

5.2: macroporous polystyrenebound cyanoborohydride resin; AcOH / CH₂Cl₂; methanol / 15 h / 70 °C

With hydrogenchloride; palladium diacetate; hydrogen; caesium carbonate; Dess-Martin periodane; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; nickel; In tetrahydrofuran; 1,4-dioxane; pyridine; methanol; dichloromethane; N,N-dimethyl acetamide; ethyl acetate; 1.1: Buchwald reaction;

DOI:10.1021/jm0601001

Reference yield:

2-(benzhydrylidene-amino)-5,6,7,8-tetrahydronaphthalene-1-carboxylic acid methyl ester (900492-90-2) → methyl 2-({[2-({2-[(2S)-(N-tert-butoxycarbonyl)pyrrolidin-2-yl]ethyl}amino)phenyl]sulfonyl}amino)-5,6,7,8-tetrahydro-1-naphthalenecarboxylate (904680-11-1)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 100 percent / aq. HCl / tetrahydrofuran / 1 h / 20 °C

2.1: pyridine / 20 °C

3.1: 1.8750 g / H₂ / Raney nickel / methanol; ethyl acetate / 2 h / 3102.89 Torr

4.1: Dess-Martin periodinane / N,N-dimethyl-acetamide; CH₂Cl₂ / 0.25 h

4.2: macroporous polystyrenebound cyanoborohydride resin; AcOH / CH₂Cl₂; methanol / 15 h / 70 °C

With hydrogenchloride; hydrogen; Dess-Martin periodane; nickel; In tetrahydrofuran; pyridine; methanol; dichloromethane; N,N-dimethyl acetamide; ethyl acetate;

DOI:10.1021/jm0601001

Reference yield:

methyl 2-{[(2-nitrophenyl)sulfonyl]amino}-5,6,7,8-tetrahydro-1-naphthalenecarboxylate (681247-34-7) → methyl 2-({[2-({2-[(2S)-(N-tert-butoxycarbonyl)pyrrolidin-2-yl]ethyl}amino)phenyl]sulfonyl}amino)-5,6,7,8-tetrahydro-1-naphthalenecarboxylate (904680-11-1)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 1.8750 g / H₂ / Raney nickel / methanol; ethyl acetate / 2 h / 3102.89 Torr

2.1: Dess-Martin periodinane / N,N-dimethyl-acetamide; CH₂Cl₂ / 0.25 h

2.2: macroporous polystyrenebound cyanoborohydride resin; AcOH / CH₂Cl₂; methanol / 15 h / 70 °C

With hydrogen; Dess-Martin periodane; nickel; In methanol; dichloromethane; N,N-dimethyl acetamide; ethyl acetate;

DOI:10.1021/jm0601001

upstream raw materials:

methyl 2-{[(2-aminophenyl)sulfonyl]amino}-5,6,7,8-tetrahydro-1-naphthalenecarboxylate

(2S)-tert-butyl 2-(2-hydroxyethyl)pyrrolidine-1-carboxylate

2-trifluoromethanesulfonyloxy-5,6,7,8-tetrahydronaphthalene-1-carboxylic acid methyl ester

2-(benzhydrylidene-amino)-5,6,7,8-tetrahydronaphthalene-1-carboxylic acid methyl ester

Downstream raw materials:

methyl 2-({[2-({2-[(2S)-2-pyrrolidinyl]ethyl}amino)phenyl]sulfonyl}amino)-5,6,7,8-tetrahydro-1-naphthalenecarboxylate

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