5-[2-amino-3-(4-azidophenyl)propionylamino]pentanoic acid {4-[3-(3-hydroxy-3-phenylpropyl)-2-(4-methoxyphenyl)-4-oxoazetidin-1-yl]phenyl}amide

Base Information

• Chemical Name: 5-[2-amino-3-(4-azidophenyl)propionylamino]pentanoic acid {4-[3-(3-hydroxy-3-phenylpropyl)-2-(4-methoxyphenyl)-4-oxoazetidin-1-yl]phenyl}amide
• CAS No.: 659733-70-7
• Molecular Formula: C₃₉H₄₃N₇O₅
• Molecular Weight: 689.814

Synonyms:5-[2-amino-3-(4-azidophenyl)propionylamino]pentanoic acid {4-[3-(3-hydroxy-3-phenylpropyl)-2-(4-methoxyphenyl)-4-oxoazetidin-1-yl]phenyl}amide

Chemical Property of 5-[2-amino-3-(4-azidophenyl)propionylamino]pentanoic acid {4-[3-(3-hydroxy-3-phenylpropyl)-2-(4-methoxyphenyl)-4-oxoazetidin-1-yl]phenyl}amide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 5-[2-amino-3-(4-azidophenyl)propionylamino]pentanoic acid {4-[3-(3-hydroxy-3-phenylpropyl)-2-(4-methoxyphenyl)-4-oxoazetidin-1-yl]phenyl}amide

There total 8 articles about 5-[2-amino-3-(4-azidophenyl)propionylamino]pentanoic acid {4-[3-(3-hydroxy-3-phenylpropyl)-2-(4-methoxyphenyl)-4-oxoazetidin-1-yl]phenyl}amide 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: 19.0%

[(S)-2-(4-Azido-phenyl)-1-(4-{4-[3-((S)-3-hydroxy-3-phenyl-propyl)-2-(4-methoxy-phenyl)-4-oxo-azetidin-1-yl]-phenylcarbamoyl}-butylcarbamoyl)-ethyl]-carbamic acid 9H-fluoren-9-ylmethyl ester (659733-69-4) → 5-[2-amino-3-(4-azidophenyl)propionylamino]pentanoic acid {4-[3-(3-hydroxy-3-phenylpropyl)-2-(4-methoxyphenyl)-4-oxoazetidin-1-yl]phenyl}amide (659733-70-7)

Guidance literature:

With diethylamine; In N,N-dimethyl-formamide; at 20 ℃; for 1h;

DOI:10.1016/S0968-0896(03)00047-6

Reference yield:

(E)-N-(4-methoxybenzylidene)-4-nitroaniline (97221-15-3) → 5-[2-amino-3-(4-azidophenyl)propionylamino]pentanoic acid {4-[3-(3-hydroxy-3-phenylpropyl)-2-(4-methoxyphenyl)-4-oxoazetidin-1-yl]phenyl}amide (659733-70-7)

Guidance literature:

Multi-step reaction with 7 steps

1.1: (i-Pr)2NEt; TMSCl; TiCl₄ / CH₂Cl₂ / 15 h / -30 - -10 °C

1.2: 3.3 g / bistrimethylsilylacetamide; tetrabutylammonium fluoride / various solvent(s) / 10 h / 20 °C

2.1: 86 percent / H₂ / Pd/C / ethyl acetate / 2 h / 3750.3 Torr

3.1: 1.1 g / HCl / H₂O; tetrahydrofuran / 2 h / 20 °C

4.1: 41 percent / TOTU; hydroxyiminocyanoacetic acid ethyl ester; N-ethylmorpholine / dimethylformamide / 1 h / 20 °C

5.1: 56 percent / Et₂NH / dimethylformamide / 1 h / 20 °C

6.1: 82 percent / TOTU; hydroxyiminocyanoacetic acid ethyl ester; N-ethylmorpholine / dimethylformamide / 1 h / 20 °C

7.1: 19 percent / Et₂NH / dimethylformamide / 1 h / 20 °C

With N-ethylmorpholine;; hydrogenchloride; chloro-trimethyl-silane; O-[(ethoxycarbonyl)cyanomethyleneamino]-N,N,N',N'-tetramethyluronium tetrafluoroborate; hydrogen; titanium tetrachloride; diethylamine; N-ethyl-N,N-diisopropylamine; ethyl cyanoglyoxylate-2-oxime; palladium on activated charcoal; In tetrahydrofuran; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1016/S0968-0896(03)00047-6

Reference yield:

5'-(S)-tert-butyldimethylsilyloxy-5'-(phenyl) valeroyl-5-(S)-phenyloxazolidinone → 5-[2-amino-3-(4-azidophenyl)propionylamino]pentanoic acid {4-[3-(3-hydroxy-3-phenylpropyl)-2-(4-methoxyphenyl)-4-oxoazetidin-1-yl]phenyl}amide (659733-70-7)

Guidance literature:

Multi-step reaction with 7 steps

1.1: (i-Pr)2NEt; TMSCl; TiCl₄ / CH₂Cl₂ / 15 h / -30 - -10 °C

1.2: 3.3 g / bistrimethylsilylacetamide; tetrabutylammonium fluoride / various solvent(s) / 10 h / 20 °C

2.1: 86 percent / H₂ / Pd/C / ethyl acetate / 2 h / 3750.3 Torr

3.1: 1.1 g / HCl / H₂O; tetrahydrofuran / 2 h / 20 °C

4.1: 41 percent / TOTU; hydroxyiminocyanoacetic acid ethyl ester; N-ethylmorpholine / dimethylformamide / 1 h / 20 °C

5.1: 56 percent / Et₂NH / dimethylformamide / 1 h / 20 °C

6.1: 82 percent / TOTU; hydroxyiminocyanoacetic acid ethyl ester; N-ethylmorpholine / dimethylformamide / 1 h / 20 °C

7.1: 19 percent / Et₂NH / dimethylformamide / 1 h / 20 °C

With N-ethylmorpholine;; hydrogenchloride; chloro-trimethyl-silane; O-[(ethoxycarbonyl)cyanomethyleneamino]-N,N,N',N'-tetramethyluronium tetrafluoroborate; hydrogen; titanium tetrachloride; diethylamine; N-ethyl-N,N-diisopropylamine; ethyl cyanoglyoxylate-2-oxime; palladium on activated charcoal; In tetrahydrofuran; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1016/S0968-0896(03)00047-6

upstream raw materials:

[(S)-2-(4-Azido-phenyl)-1-(4-{4-[3-((S)-3-hydroxy-3-phenyl-propyl)-2-(4-methoxy-phenyl)-4-oxo-azetidin-1-yl]-phenylcarbamoyl}-butylcarbamoyl)-ethyl]-carbamic acid 9H-fluoren-9-ylmethyl ester

(E)-N-(4-methoxybenzylidene)-4-nitroaniline

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