1-[(N-methyl-N-benzyloxycarbonyl)amino]-3-[(N-acetyl-L-phenylalanyl)amino]-2-azetidinone

Base Information

Chemical Name:1-[(N-methyl-N-benzyloxycarbonyl)amino]-3-[(N-acetyl-L-phenylalanyl)amino]-2-azetidinone
CAS No.:485831-59-2
Molecular Formula:C₂₃H₂₆N₄O₅
Molecular Weight:438.483
Hs Code.:

Synonyms:1-[(N-methyl-N-benzyloxycarbonyl)amino]-3-[(N-acetyl-L-phenylalanyl)amino]-2-azetidinone

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Chemical Property of 1-[(N-methyl-N-benzyloxycarbonyl)amino]-3-[(N-acetyl-L-phenylalanyl)amino]-2-azetidinone

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Technology Process of 1-[(N-methyl-N-benzyloxycarbonyl)amino]-3-[(N-acetyl-L-phenylalanyl)amino]-2-azetidinone

There total 5 articles about 1-[(N-methyl-N-benzyloxycarbonyl)amino]-3-[(N-acetyl-L-phenylalanyl)amino]-2-azetidinone 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: 74.0%

: 2018-61-3
(S)-2-acetylamino-3-phenylpropanoic acid

: 1-[(N-methyl-N-benzyloxycarbonyl)amino]-3-amino-2-azetidinone hydrochloride

: 485831-59-2
1-[(N-methyl-N-benzyloxycarbonyl)amino]-3-[(N-acetyl-L-phenylalanyl)amino]-2-azetidinone

Guidance literature:: With 1-hydroxy-7-aza-benzotriazole; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; In N,N-dimethyl-formamide; at 0 - 20 ℃;
DOI:10.1021/jo026280d

Reference yield:

: 37519-04-3
1-(benzyloxy)carbonyl-1-methylhydrazine

: 485831-59-2
1-[(N-methyl-N-benzyloxycarbonyl)amino]-3-[(N-acetyl-L-phenylalanyl)amino]-2-azetidinone

Guidance literature:: Multi-step reaction with 4 steps

1: 67 percent / EEDQ / CH₂Cl₂ / -12 - 20 °C

2: 88 percent / PPh₃; DBAD / tetrahydrofuran / 20 °C

3: 99 percent / 3.0 M HCl / ethyl acetate / 0.5 h / 20 °C

4: 74 percent / EDC; 1-hydroxy-7-azabenzotriazole; Et₃N / dimethylformamide / 0 - 20 °C

With hydrogenchloride; 1-hydroxy-7-aza-benzotriazole; dibenzyl azodicarboxylate; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline; triethylamine; triphenylphosphine; In tetrahydrofuran; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; 2: Mitsunobu reaction;
DOI:10.1021/jo026280d

Reference yield:

: 501-53-1,94274-21-2
benzyl chloroformate

: 485831-59-2
1-[(N-methyl-N-benzyloxycarbonyl)amino]-3-[(N-acetyl-L-phenylalanyl)amino]-2-azetidinone

Guidance literature:: Multi-step reaction with 5 steps

1: 55 percent / NaOH / CH₂Cl₂ / 4 h / 20 °C

2: 67 percent / EEDQ / CH₂Cl₂ / -12 - 20 °C

3: 88 percent / PPh₃; DBAD / tetrahydrofuran / 20 °C

4: 99 percent / 3.0 M HCl / ethyl acetate / 0.5 h / 20 °C

5: 74 percent / EDC; 1-hydroxy-7-azabenzotriazole; Et₃N / dimethylformamide / 0 - 20 °C

With hydrogenchloride; sodium hydroxide; 1-hydroxy-7-aza-benzotriazole; dibenzyl azodicarboxylate; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline; triethylamine; triphenylphosphine; In tetrahydrofuran; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; 3: Mitsunobu reaction;
DOI:10.1021/jo026280d