(S)-2-Benzyl-4-oxo-azetidine-1-carboxylic acid methyl-(4-nitro-benzyl)-amide

Base Information

• Chemical Name: (S)-2-Benzyl-4-oxo-azetidine-1-carboxylic acid methyl-(4-nitro-benzyl)-amide
• CAS No.: 211619-17-9
• Molecular Formula: C₁₉H₁₉N₃O₄
• Molecular Weight: 353.378
• Mol file: 211619-17-9.mol

Synonyms:(S)-2-Benzyl-4-oxo-azetidine-1-carboxylic acid methyl-(4-nitro-benzyl)-amide

Chemical Property of (S)-2-Benzyl-4-oxo-azetidine-1-carboxylic acid methyl-(4-nitro-benzyl)-amide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-2-Benzyl-4-oxo-azetidine-1-carboxylic acid methyl-(4-nitro-benzyl)-amide

There total 7 articles about (S)-2-Benzyl-4-oxo-azetidine-1-carboxylic acid methyl-(4-nitro-benzyl)-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:

N-Cbz-L-Phe (1161-13-3) → (S)-2-Benzyl-4-oxo-azetidine-1-carboxylic acid methyl-(4-nitro-benzyl)-amide (211619-17-9)

Guidance literature:

Multi-step reaction with 6 steps

1: Et₃N / 13 °C / 1.) -10 deg C, 20 min, 2.) RT, 30 min

2: diethyl ether / 0.17 h / Ambient temperature

3: 63 percent / silver benzoate, Et₃N / 0.5 h / Ambient temperature

4: 93 percent / H₂ / 20percent Pd(OH)2/C / methanol / 7 h / 760 Torr / Ambient temperature

5: 54 percent / NaHCO₃, MsCl / acetonitrile / 16 h / Heating

6: 1.) potassium bis(trimethylsilyl)amide / 1.) THF, toluene, -5 deg C, 20 min, 2.) THF, toluene, from -78 deg C to -20 deg C, 2 h

With hydrogen; silver benzoate; potassium hexamethylsilazane; sodium hydrogencarbonate; methanesulfonyl chloride; triethylamine; palladium dihydroxide; In methanol; diethyl ether; acetonitrile;

DOI:10.1021/jm980131z

Reference yield:

(S)-3-[(benzyloxycarbonyl)amino]-1-diazo-4-phenyl-2-butanone (15196-02-8) → (S)-2-Benzyl-4-oxo-azetidine-1-carboxylic acid methyl-(4-nitro-benzyl)-amide (211619-17-9)

Guidance literature:

Multi-step reaction with 4 steps

1: 63 percent / silver benzoate, Et₃N / 0.5 h / Ambient temperature

2: 93 percent / H₂ / 20percent Pd(OH)2/C / methanol / 7 h / 760 Torr / Ambient temperature

3: 54 percent / NaHCO₃, MsCl / acetonitrile / 16 h / Heating

4: 1.) potassium bis(trimethylsilyl)amide / 1.) THF, toluene, -5 deg C, 20 min, 2.) THF, toluene, from -78 deg C to -20 deg C, 2 h

With hydrogen; silver benzoate; potassium hexamethylsilazane; sodium hydrogencarbonate; methanesulfonyl chloride; triethylamine; palladium dihydroxide; In methanol; acetonitrile;

DOI:10.1021/jm980131z

Reference yield:

Z-Phe-O-COO-isoBu (41518-17-6) → (S)-2-Benzyl-4-oxo-azetidine-1-carboxylic acid methyl-(4-nitro-benzyl)-amide (211619-17-9)

Guidance literature:

Multi-step reaction with 5 steps

1: diethyl ether / 0.17 h / Ambient temperature

2: 63 percent / silver benzoate, Et₃N / 0.5 h / Ambient temperature

3: 93 percent / H₂ / 20percent Pd(OH)2/C / methanol / 7 h / 760 Torr / Ambient temperature

4: 54 percent / NaHCO₃, MsCl / acetonitrile / 16 h / Heating

5: 1.) potassium bis(trimethylsilyl)amide / 1.) THF, toluene, -5 deg C, 20 min, 2.) THF, toluene, from -78 deg C to -20 deg C, 2 h

With hydrogen; silver benzoate; potassium hexamethylsilazane; sodium hydrogencarbonate; methanesulfonyl chloride; triethylamine; palladium dihydroxide; In methanol; diethyl ether; acetonitrile;

DOI:10.1021/jm980131z

upstream raw materials:

C₉H₉ClN₂O₃

(S)-4-benzyl-2-azetidinone

N-Cbz-L-Phe

(S)-3-[(benzyloxycarbonyl)amino]-1-diazo-4-phenyl-2-butanone