ethyl [4-[1-[3-methoxy-4-[N'-(2-methylphenyl)ureido]phenylacetyl]-(3R,4S)-isopropylidenedioxy-(2S)-pyrrolidinylcarbonyl]-1-piperazinyl]acetate

Base Information

Chemical Name:ethyl [4-[1-[3-methoxy-4-[N'-(2-methylphenyl)ureido]phenylacetyl]-(3R,4S)-isopropylidenedioxy-(2S)-pyrrolidinylcarbonyl]-1-piperazinyl]acetate
CAS No.:317354-96-4
Molecular Formula:C₃₃H₄₃N₅O₈
Molecular Weight:637.733
Hs Code.:

Synonyms:ethyl [4-[1-[3-methoxy-4-[N'-(2-methylphenyl)ureido]phenylacetyl]-(3R,4S)-isopropylidenedioxy-(2S)-pyrrolidinylcarbonyl]-1-piperazinyl]acetate

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Chemical Property of ethyl [4-[1-[3-methoxy-4-[N'-(2-methylphenyl)ureido]phenylacetyl]-(3R,4S)-isopropylidenedioxy-(2S)-pyrrolidinylcarbonyl]-1-piperazinyl]acetate

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Technology Process of ethyl [4-[1-[3-methoxy-4-[N'-(2-methylphenyl)ureido]phenylacetyl]-(3R,4S)-isopropylidenedioxy-(2S)-pyrrolidinylcarbonyl]-1-piperazinyl]acetate

There total 10 articles about ethyl [4-[1-[3-methoxy-4-[N'-(2-methylphenyl)ureido]phenylacetyl]-(3R,4S)-isopropylidenedioxy-(2S)-pyrrolidinylcarbonyl]-1-piperazinyl]acetate 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: 92.0%

: 886447-38-7
ethyl [4-[(3R,4S)-isopropylidenedioxy-(2S)-pyrrolidinylcarbonyl]-1-piperazinyl]acetate

: 181519-21-1
3-methoxy-4-[N'-(2-methylphenyl)ureido]phenylacetic acid

: 317354-96-4
ethyl [4-[1-[3-methoxy-4-[N'-(2-methylphenyl)ureido]phenylacetyl]-(3R,4S)-isopropylidenedioxy-(2S)-pyrrolidinylcarbonyl]-1-piperazinyl]acetate

Guidance literature:: With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In tetrahydrofuran; at 20 ℃; for 12h;
DOI:10.1016/j.bmc.2005.11.058

Reference yield:

: methyl 1-benzyloxycarbonyl-3(RS),4(SR)-dihydroxy-2(S)-pyrrolidinylcarboxylate

: 317354-96-4
ethyl [4-[1-[3-methoxy-4-[N'-(2-methylphenyl)ureido]phenylacetyl]-(3R,4S)-isopropylidenedioxy-(2S)-pyrrolidinylcarbonyl]-1-piperazinyl]acetate

Guidance literature:: Multi-step reaction with 5 steps

1: 89 percent / p-TsOH*H₂O / CH₂Cl₂ / 1 h / 20 °C

2: 91 percent / aq. NaOH / tetrahydrofuran; methanol / 24 h / 20 °C

3: 79 percent / 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide HCl salt; HOBt; Et₃N / CH₂Cl₂ / 12 h / 20 °C

4: 90 percent / hydrogen / Pd/C / ethanol / 10 h / 20 °C

5: 92 percent / 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide HCl salt; HOBt; Et₃N / tetrahydrofuran / 12 h / 20 °C

With sodium hydroxide; hydrogen; benzotriazol-1-ol; toluene-4-sulfonic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; dichloromethane;
DOI:10.1016/j.bmc.2005.11.058

Reference yield:

: 886447-82-1
ethyl [4-[N-benzyloxycarbonyl-(3R,4S)-isopropylidenedioxy-(2S)-pyrrolidinylcarbonyl]-1-piperazinyl]acetate

: 317354-96-4
ethyl [4-[1-[3-methoxy-4-[N'-(2-methylphenyl)ureido]phenylacetyl]-(3R,4S)-isopropylidenedioxy-(2S)-pyrrolidinylcarbonyl]-1-piperazinyl]acetate

Guidance literature:: Multi-step reaction with 2 steps

1: 90 percent / hydrogen / Pd/C / ethanol / 10 h / 20 °C

2: 92 percent / 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide HCl salt; HOBt; Et₃N / tetrahydrofuran / 12 h / 20 °C

With hydrogen; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; palladium on activated charcoal; In tetrahydrofuran; ethanol;
DOI:10.1016/j.bmc.2005.11.058