cis-5-[((1R,2S)-1-tert-butoxycarbonyl-2-vinylcyclopropyl)carbamoyl]-3-hydroxycyclopent-1-enecarboxylic acid methyl ester

Base Information

Chemical Name:cis-5-[((1R,2S)-1-tert-butoxycarbonyl-2-vinylcyclopropyl)carbamoyl]-3-hydroxycyclopent-1-enecarboxylic acid methyl ester
CAS No.:862174-36-5
Molecular Formula:C₁₈H₂₅NO₆
Molecular Weight:351.4
Hs Code.:

Synonyms:cis-5-[((1R,2S)-1-tert-butoxycarbonyl-2-vinylcyclopropyl)carbamoyl]-3-hydroxycyclopent-1-enecarboxylic acid methyl ester

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Chemical Property of cis-5-[((1R,2S)-1-tert-butoxycarbonyl-2-vinylcyclopropyl)carbamoyl]-3-hydroxycyclopent-1-enecarboxylic acid methyl ester

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Technology Process of cis-5-[((1R,2S)-1-tert-butoxycarbonyl-2-vinylcyclopropyl)carbamoyl]-3-hydroxycyclopent-1-enecarboxylic acid methyl ester

There total 1 articles about cis-5-[((1R,2S)-1-tert-butoxycarbonyl-2-vinylcyclopropyl)carbamoyl]-3-hydroxycyclopent-1-enecarboxylic acid methyl ester 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:

: 746657-36-3,213316-32-6,259221-73-3
(1R,2S)-ethyl 1-amino-2-vinylcyclopropanecarboxylate

: 862174-36-5
cis-5-[((1R,2S)-1-tert-butoxycarbonyl-2-vinylcyclopropyl)carbamoyl]-3-hydroxycyclopent-1-enecarboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: 100 percent / LiOH / H₂O; dioxane / 24 h / 0 °C

2: 75 percent / NaHCO₃ / H₂O; dioxane / 0 - 20 °C

3: 76 percent / CH₂Cl₂ / 48 h / 50 °C

4: 22 percent / piperidine / dimethylformamide / 1 h / 0 °C

5: O-(7-azabenzotriazol-1-yl)-N,N,N',N'-tetramethyluronium PF₆; ethyldiisopropylamine / dimethylformamide / cooling

With piperidine; lithium hydroxide; sodium hydrogencarbonate; N-ethyl-N,N-diisopropylamine; HATU; In 1,4-dioxane; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1016/j.bmc.2006.10.044

Reference yield: 78.0%

: 862174-36-5
cis-5-[((1R,2S)-1-tert-butoxycarbonyl-2-vinylcyclopropyl)carbamoyl]-3-hydroxycyclopent-1-enecarboxylic acid methyl ester

: 20430-72-2,189816-04-4
7-methoxy-2-phenylquinolin-4-ol

: 862174-39-8
trans-5-[((1R,2S)-1-tert-butoxycarbonyl-1-vinylcyclopropyl)carbamoyl]-3-(7-methoxy-2-phenylquinolin-4-yloxy)cyclopent-1-enecarboxylic acid methyl ester

Guidance literature:: With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; cooling;
DOI:10.1016/j.bmc.2006.10.044

Reference yield:

: 862174-36-5
cis-5-[((1R,2S)-1-tert-butoxycarbonyl-2-vinylcyclopropyl)carbamoyl]-3-hydroxycyclopent-1-enecarboxylic acid methyl ester

: trans-5-[((1R,2S)-1-tert-butoxycarbonyl-1-vinylcyclopropyl)carbamoyl]-3-(7-methoxy-2-phenylquinolin-4-yloxy)cyclopent-1-enecarboxylic acid lithium salt

Guidance literature:: Multi-step reaction with 2 steps

1: 78 percent / triphenylphosphine; diisopropyl azodicarboxylate / tetrahydrofuran / cooling

2: 97 percent / aq. LiOH / dioxane

With lithium hydroxide; di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; 1,4-dioxane;
DOI:10.1016/j.bmc.2006.10.044