1,1-dimethylethyl (2S,4S)-2-[({(1R,2S)-2-ethenyl-1-[(ethyloxy)carbonyl]cyclopropyl}amino)carbonyl]-4-hydroxy-1-pyrrolidinecarboxylate

Base Information

• Chemical Name: 1,1-dimethylethyl (2S,4S)-2-[({(1R,2S)-2-ethenyl-1-[(ethyloxy)carbonyl]cyclopropyl}amino)carbonyl]-4-hydroxy-1-pyrrolidinecarboxylate
• CAS No.: 960390-07-2
• Molecular Formula: C₁₈H₂₈N₂O₆
• Molecular Weight: 368.43
• Mol file: 960390-07-2.mol

Synonyms:1,1-dimethylethyl (2S,4S)-2-[({(1R,2S)-2-ethenyl-1-[(ethyloxy)carbonyl]cyclopropyl}amino)carbonyl]-4-hydroxy-1-pyrrolidinecarboxylate

Chemical Property of 1,1-dimethylethyl (2S,4S)-2-[({(1R,2S)-2-ethenyl-1-[(ethyloxy)carbonyl]cyclopropyl}amino)carbonyl]-4-hydroxy-1-pyrrolidinecarboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1,1-dimethylethyl (2S,4S)-2-[({(1R,2S)-2-ethenyl-1-[(ethyloxy)carbonyl]cyclopropyl}amino)carbonyl]-4-hydroxy-1-pyrrolidinecarboxylate

There total 2 articles about 1,1-dimethylethyl (2S,4S)-2-[({(1R,2S)-2-ethenyl-1-[(ethyloxy)carbonyl]cyclopropyl}amino)carbonyl]-4-hydroxy-1-pyrrolidinecarboxylate 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: 95.0%

ethyl (1R,2S)-1-amino-2-vinylcyclopropanecarboxylate hydrochloride (259214-54-5,259214-56-7) + N-tert-butoxycarbonyl-L-cis-4-hydroxyproline (87691-27-8,946610-68-0) → 1,1-dimethylethyl (2S,4S)-2-[({(1R,2S)-2-ethenyl-1-[(ethyloxy)carbonyl]cyclopropyl}amino)carbonyl]-4-hydroxy-1-pyrrolidinecarboxylate (960390-07-2)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; HATU; In dichloromethane; at 0 - 20 ℃; Inert atmosphere;

Reference yield: 78.0%

(1R,2S)-1-amino-2-vinylcyclopropanecarboxylic acid ethyl ester tosylate salt (1159609-95-6) + N-tert-butoxycarbonyl-L-cis-4-hydroxyproline (87691-27-8,946610-68-0) → 1,1-dimethylethyl (2S,4S)-2-[({(1R,2S)-2-ethenyl-1-[(ethyloxy)carbonyl]cyclopropyl}amino)carbonyl]-4-hydroxy-1-pyrrolidinecarboxylate (960390-07-2)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; HATU; In N,N-dimethyl-formamide; at 0 ℃; for 0.883333h; Inert atmosphere;

Reference yield:

1,1-dimethylethyl (2S,4S)-2-[({(1R,2S)-2-ethenyl-1-[(ethyloxy)carbonyl]cyclopropyl}amino)carbonyl]-4-hydroxy-1-pyrrolidinecarboxylate (960390-07-2) → (2R,6S,13aS,14aR,16aS)-N-(cyclopropylsulfonyl)-2-{[8-methyl-2-[4-(1-methylethyl)-1,3-thiazol-2-yl]-7-(methyloxy)-4-quinolinyl]oxy}-5,16-dioxo-6-{[(4-phenyl-1-piperidinyl)carbonyl]amino}-1,2,3,6,7,8,9,10,11,13a,14,15,16,16a-tetradecahydrocyclopropa[e]pyrrolo[1,2-a][1,4]diazacyclopentadecine-14a(5H)-carboxamide

Guidance literature:

Multi-step reaction with 8 steps

1.1: hydrogenchloride / 1,4-dioxane; dichloromethane; water / 1.5 h / 20 °C / Inert atmosphere

2.1: N-ethyl-N,N-diisopropylamine; HATU / dichloromethane / 4 h / 0 - 20 °C / Inert atmosphere

3.1: 1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidene[2-(iso-propoxy)-5-(N,N-dimethylaminosulfonyl)phenyl]methylene ruthenium(II) dichloride / 1,2-dichloro-ethane / 21 h / 75 °C / Inert atmosphere

4.1: di-isopropyl azodicarboxylate; triphenylphosphine / tetrahydrofuran; toluene / 18 h / 0 - 20 °C / Inert atmosphere

5.1: lithium hydroxide / tetrahydrofuran; methanol; water / 18 h / 20 °C / Inert atmosphere

6.1: 1,1'-carbonyldiimidazole / N,N-dimethyl-formamide / 1 h / 40 °C / Inert atmosphere

6.2: 18 h / 40 °C / Inert atmosphere

7.1: hydrogenchloride / 1,4-dioxane; water; ethyl acetate; N,N-dimethyl-formamide / 3 h / Inert atmosphere

8.1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 0 - 20 °C / Inert atmosphere

8.2: Inert atmosphere

With hydrogenchloride; 1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidene[2-(iso-propoxy)-5-(N,N-dimethylaminosulfonyl)phenyl]methylene ruthenium(II) dichloride; di-isopropyl azodicarboxylate; N-ethyl-N,N-diisopropylamine; triphenylphosphine; HATU; 1,1'-carbonyldiimidazole; lithium hydroxide; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; water; ethyl acetate; 1,2-dichloro-ethane; N,N-dimethyl-formamide; toluene;

DOI:10.1021/jm201278q

upstream raw materials:

ethyl (1R,2S)-1-amino-2-vinylcyclopropanecarboxylate hydrochloride

N-tert-butoxycarbonyl-L-cis-4-hydroxyproline

(1R,2S)-1-amino-2-vinylcyclopropanecarboxylic acid ethyl ester tosylate salt