(7S)-1⁴-Methoxycarbonyl-7-tert-butoxycarbonylamino-6-oxo-5-aza-1⁽¹⁾,3(1,4)-dibenzenanonaphane-9-carboxylic acid

Base Information

• Chemical Name: (7S)-1⁴-Methoxycarbonyl-7-tert-butoxycarbonylamino-6-oxo-5-aza-1⁽¹⁾,3(1,4)-dibenzenanonaphane-9-carboxylic acid
• CAS No.: 276241-96-4
• Molecular Formula: C₂₆H₃₂N₂O₇
• Molecular Weight: 484.549

Synonyms:(7S)-1⁴-Methoxycarbonyl-7-tert-butoxycarbonylamino-6-oxo-5-aza-1⁽¹⁾,3(1,4)-dibenzenanonaphane-9-carboxylic acid

Chemical Property of (7S)-1⁴-Methoxycarbonyl-7-tert-butoxycarbonylamino-6-oxo-5-aza-1⁽¹⁾,3(1,4)-dibenzenanonaphane-9-carboxylic acid

Chemical Property:

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Technology Process of (7S)-1⁴-Methoxycarbonyl-7-tert-butoxycarbonylamino-6-oxo-5-aza-1⁽¹⁾,3(1,4)-dibenzenanonaphane-9-carboxylic acid

There total 3 articles about (7S)-1⁴-Methoxycarbonyl-7-tert-butoxycarbonylamino-6-oxo-5-aza-1⁽¹⁾,3(1,4)-dibenzenanonaphane-9-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: 95.0%

9-Allyl 1-methyl (7S)-7-(tert-butoxycarbonylamino)-6-oxo-5-aza-1(1),3(1,4)-dibenzenanonaphane-14,9-dicarboxylate (276241-95-3) → (7S)-14-Methoxycarbonyl-7-tert-butoxycarbonylamino-6-oxo-5-aza-1(1),3(1,4)-dibenzenanonaphane-9-carboxylic acid (276241-96-4)

Guidance literature:

With pyrrolidine; triphenylphosphine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In dichloromethane; for 0.5h;

DOI:10.1039/a908090b

Reference yield:

N-α-(t-butoxycarbonyl)-L-glutamic γ-allyl ester (132286-79-4,259221-91-5) → (7S)-14-Methoxycarbonyl-7-tert-butoxycarbonylamino-6-oxo-5-aza-1(1),3(1,4)-dibenzenanonaphane-9-carboxylic acid (276241-96-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 67 percent / DCC; HOBT; ethyl diisopropyl amine / dimethylformamide / 24 h / 20 °C

2: 95 percent / pyrrolidine; PPh₃ / Pd(PPh₃)4 / CH₂Cl₂ / 0.5 h

With pyrrolidine; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; triphenylphosphine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In dichloromethane; N,N-dimethyl-formamide; 1: Acylation / 2: dealkylation;

DOI:10.1039/a908090b

Reference yield:

4-(4-Aminomethyl-benzyl)-benzoic acid methyl ester; hydrochloride → (7S)-14-Methoxycarbonyl-7-tert-butoxycarbonylamino-6-oxo-5-aza-1(1),3(1,4)-dibenzenanonaphane-9-carboxylic acid (276241-96-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 67 percent / DCC; HOBT; ethyl diisopropyl amine / dimethylformamide / 24 h / 20 °C

2: 95 percent / pyrrolidine; PPh₃ / Pd(PPh₃)4 / CH₂Cl₂ / 0.5 h

With pyrrolidine; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; triphenylphosphine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In dichloromethane; N,N-dimethyl-formamide; 1: Acylation / 2: dealkylation;

DOI:10.1039/a908090b

upstream raw materials:

9-Allyl 1-methyl (7S)-7-(tert-butoxycarbonylamino)-6-oxo-5-aza-1⁽¹⁾,3(1,4)-dibenzenanonaphane-1⁴,9-dicarboxylate

N-α-(t-butoxycarbonyl)-L-glutamic γ-allyl ester

Downstream raw materials:

(7S,12S,18S,23S)-Dimethyl 12,18-dibenzyl-7,23-bis(tert-butoxycarbonylamino)-6,10,13,17,20,24-hexaoxo-5,11,14,16,19,25-hexaaza-15(2,6)-pyridina-1,29⁽¹⁾,3,27(1,4)-tetrabenzenanonacosaphane-1⁴,29⁴-dicarboxylate

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