(4S,7S)-7-Benzyl-4-diallylamino-15-nitro-2-oxa-6,9-diaza-bicyclo[10.2.2]hexadeca-1⁽¹⁵⁾,12⁽¹⁶⁾,13-triene-5,8-dione

Base Information

• Chemical Name: (4S,7S)-7-Benzyl-4-diallylamino-15-nitro-2-oxa-6,9-diaza-bicyclo[10.2.2]hexadeca-1⁽¹⁵⁾,12⁽¹⁶⁾,13-triene-5,8-dione
• CAS No.: 185394-04-1
• Molecular Formula: C₂₆H₃₀N₄O₅
• Molecular Weight: 478.548

Synonyms:(4S,7S)-7-Benzyl-4-diallylamino-15-nitro-2-oxa-6,9-diaza-bicyclo[10.2.2]hexadeca-1⁽¹⁵⁾,12⁽¹⁶⁾,13-triene-5,8-dione

Chemical Property of (4S,7S)-7-Benzyl-4-diallylamino-15-nitro-2-oxa-6,9-diaza-bicyclo[10.2.2]hexadeca-1⁽¹⁵⁾,12⁽¹⁶⁾,13-triene-5,8-dione

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Technology Process of (4S,7S)-7-Benzyl-4-diallylamino-15-nitro-2-oxa-6,9-diaza-bicyclo[10.2.2]hexadeca-1⁽¹⁵⁾,12⁽¹⁶⁾,13-triene-5,8-dione

There total 7 articles about (4S,7S)-7-Benzyl-4-diallylamino-15-nitro-2-oxa-6,9-diaza-bicyclo[10.2.2]hexadeca-1⁽¹⁵⁾,12⁽¹⁶⁾,13-triene-5,8-dione 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: 66.0%

(S)-2-Diallylamino-N-{(S)-1-[2-(4-fluoro-3-nitro-phenyl)-ethylcarbamoyl]-2-phenyl-ethyl}-3-hydroxy-propionamide (185394-02-9) → (4S,7S)-7-Benzyl-4-diallylamino-15-nitro-2-oxa-6,9-diaza-bicyclo[10.2.2]hexadeca-1(15),12(16),13-triene-5,8-dione (185394-04-1)

Guidance literature:

With molecular sieve; tetrabutyl ammonium fluoride; In tetrahydrofuran; N,N-dimethyl-formamide; at 20 ℃; for 5h;

DOI:10.1021/ja0170807

Reference yield:

N-tert-butoxycarbonyl-L-phenylalanine (13734-34-4) → (4S,7S)-7-Benzyl-4-diallylamino-15-nitro-2-oxa-6,9-diaza-bicyclo[10.2.2]hexadeca-1(15),12(16),13-triene-5,8-dione (185394-04-1)

Guidance literature:

Multi-step reaction with 6 steps

1: 85 percent / Et₃N; EDC; HOBt / CH₂Cl₂; dimethylformamide / 15 h / 20 °C

2: conc. HCl / acetonitrile / 2 h / 20 °C

3: 68 percent / EDC; HOBt; Et₃N / CH₂Cl₂ / 8 h / 20 °C

4: 93 percent / HCl / acetonitrile / 1 h / 20 °C

5: 70 percent / NaHCO₃ / tetrahydrofuran; dimethylsulfoxide / 4 h / 90 °C

6: 66 percent / TBAF; molecular sieves / dimethylformamide; tetrahydrofuran / 5 h / 20 °C

With hydrogenchloride; molecular sieve; tetrabutyl ammonium fluoride; sodium hydrogencarbonate; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; In tetrahydrofuran; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/ja0170807

Reference yield:

(S)-2-Amino-N-[2-(4-fluoro-3-nitro-phenyl)-ethyl]-3-phenyl-propionamide → (4S,7S)-7-Benzyl-4-diallylamino-15-nitro-2-oxa-6,9-diaza-bicyclo[10.2.2]hexadeca-1(15),12(16),13-triene-5,8-dione (185394-04-1)

Guidance literature:

Multi-step reaction with 4 steps

1: 68 percent / EDC; HOBt; Et₃N / CH₂Cl₂ / 8 h / 20 °C

2: 93 percent / HCl / acetonitrile / 1 h / 20 °C

3: 70 percent / NaHCO₃ / tetrahydrofuran; dimethylsulfoxide / 4 h / 90 °C

4: 66 percent / TBAF; molecular sieves / dimethylformamide; tetrahydrofuran / 5 h / 20 °C

With hydrogenchloride; molecular sieve; tetrabutyl ammonium fluoride; sodium hydrogencarbonate; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; In tetrahydrofuran; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/ja0170807

upstream raw materials:

(S)-2-Diallylamino-N-{(S)-1-[2-(4-fluoro-3-nitro-phenyl)-ethylcarbamoyl]-2-phenyl-ethyl}-3-hydroxy-propionamide

N-tert-butoxycarbonyl-L-phenylalanine

{(S)-1-[2-(4-Fluoro-3-nitro-phenyl)-ethylcarbamoyl]-2-phenyl-ethyl}-carbamic acid tert-butyl ester

(S)-2-Amino-N-{(S)-1-[2-(4-fluoro-3-nitro-phenyl)-ethylcarbamoyl]-2-phenyl-ethyl}-3-hydroxy-propionamide

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