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

Base Information

• Chemical Name: ethyl [4-[N-benzyloxycarbonyl-(3R,4S)-isopropylidenedioxy-(2S)-pyrrolidinylcarbonyl]-1-piperazinyl]acetate
• CAS No.: 886447-82-1
• Molecular Formula: C₂₄H₃₃N₃O₇
• Molecular Weight: 475.542

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

Chemical Property of ethyl [4-[N-benzyloxycarbonyl-(3R,4S)-isopropylidenedioxy-(2S)-pyrrolidinylcarbonyl]-1-piperazinyl]acetate

Chemical Property:

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Technology Process of ethyl [4-[N-benzyloxycarbonyl-(3R,4S)-isopropylidenedioxy-(2S)-pyrrolidinylcarbonyl]-1-piperazinyl]acetate

There total 7 articles about ethyl [4-[N-benzyloxycarbonyl-(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: 79.0%

1-benzyloxycarbonyl-(3R,4R)-isopropylidenedioxy-(2S)-pyrrolidinylcarboxylic acid sodium salt + 1-(Ethoxycarbonylmethyl)piperazine (40004-08-8) → ethyl [4-[N-benzyloxycarbonyl-(3R,4S)-isopropylidenedioxy-(2S)-pyrrolidinylcarbonyl]-1-piperazinyl]acetate (886447-82-1)

Guidance literature:

With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In dichloromethane; at 20 ℃; for 12h;

DOI:10.1016/j.bmc.2005.11.058

Reference yield:

methyl (2S,4R)-1-benzyloxycarbonyl-4-hydroxypyrrolidine-2-carboxylate (64187-48-0) → ethyl [4-[N-benzyloxycarbonyl-(3R,4S)-isopropylidenedioxy-(2S)-pyrrolidinylcarbonyl]-1-piperazinyl]acetate (886447-82-1)

Guidance literature:

Multi-step reaction with 7 steps

1: 97 percent / methyl triflate; N-methylimidazole / tetrahydrofuran / 0 - 20 °C

2: 82 percent / NaBH₄ / methanol / 5 h / Heating

3: 74 percent / H₂O₂; pyridine / CH₂Cl₂ / 0 - 20 °C

4: 95 percent / N-methylmorpholine N-oxide; H₂O / OsO₄ / acetone / 24 h / 20 °C

5: 89 percent / p-TsOH*H₂O / CH₂Cl₂ / 1 h / 20 °C

6: 91 percent / aq. NaOH / tetrahydrofuran; methanol / 24 h / 20 °C

7: 79 percent / 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide HCl salt; HOBt; Et₃N / CH₂Cl₂ / 12 h / 20 °C

With pyridine; 1-methyl-1H-imidazole; sodium hydroxide; sodium tetrahydroborate; water; dihydrogen peroxide; benzotriazol-1-ol; toluene-4-sulfonic acid; 4-methylmorpholine N-oxide; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; methyl trifluoromethanesulfonate; osmium(VIII) oxide; In tetrahydrofuran; methanol; dichloromethane; acetone;

DOI:10.1016/j.bmc.2005.11.058

Reference yield:

(2S)-2,5-dihydro-1H-pyrrole-1,2-dicarboxylic acid 2-methyl 1-(phenylmethyl) ester (5211-24-5) → ethyl [4-[N-benzyloxycarbonyl-(3R,4S)-isopropylidenedioxy-(2S)-pyrrolidinylcarbonyl]-1-piperazinyl]acetate (886447-82-1)

Guidance literature:

Multi-step reaction with 4 steps

1: 95 percent / N-methylmorpholine N-oxide; H₂O / OsO₄ / acetone / 24 h / 20 °C

2: 89 percent / p-TsOH*H₂O / CH₂Cl₂ / 1 h / 20 °C

3: 91 percent / aq. NaOH / tetrahydrofuran; methanol / 24 h / 20 °C

4: 79 percent / 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide HCl salt; HOBt; Et₃N / CH₂Cl₂ / 12 h / 20 °C

With sodium hydroxide; water; benzotriazol-1-ol; toluene-4-sulfonic acid; 4-methylmorpholine N-oxide; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; osmium(VIII) oxide; In tetrahydrofuran; methanol; dichloromethane; acetone;

DOI:10.1016/j.bmc.2005.11.058

upstream raw materials:

1-(Ethoxycarbonylmethyl)piperazine

methyl (2S,4R)-1-benzyloxycarbonyl-4-hydroxypyrrolidine-2-carboxylate

(2S)-2,5-dihydro-1H-pyrrole-1,2-dicarboxylic acid 2-methyl 1-(phenylmethyl) ester

(2S,3R,4S)-N-benzyloxycarbonyl-3,4-dihydroxyproline-3,4-isopropylidene acetal methyl ester

Downstream raw materials:

[4-((2S,3R,4S)-3,4-Dihydroxy-1-{2-[3-methoxy-4-(3-o-tolyl-ureido)-phenyl]-acetyl}-pyrrolidine-2-carbonyl)-piperazin-1-yl]-acetic acid ethyl ester

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

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