Cyclopropa[e]pyrrolo[1,2-a][1,4]diazacyclopentadecine-14a(5H)-carboxylic acid, 2-[[(4-broMophenyl)sulfonyl]oxy]-6-[[(cyclopentyloxy)carbonyl]aMino]-1,2,3,6,7,8,9,10,11,13a,14,15,16,16a-tetradecahydro-5,16-dioxo-, Methyl ester, (2S,6S,12Z,13aS,14aR,16aS)-

Base Information

• Chemical Name: Cyclopropa[e]pyrrolo[1,2-a][1,4]diazacyclopentadecine-14a(5H)-carboxylic acid, 2-[[(4-broMophenyl)sulfonyl]oxy]-6-[[(cyclopentyloxy)carbonyl]aMino]-1,2,3,6,7,8,9,10,11,13a,14,15,16,16a-tetradecahydro-5,16-dioxo-, Methyl ester, (2S,6S,12Z,13aS,14aR,16aS)-
• CAS No.: 782479-05-4
• Molecular Formula: C31H40BrN3O9S
• Molecular Weight: 711
• Mol file: 782479-05-4.mol

Synonyms:Cyclopropa[e]pyrrolo[1,2-a][1,4]diazacyclopentadecine-14a(5H)-carboxylic acid, 2-[[(4-broMophenyl)sulfonyl]oxy]-6-[[(cyclopentyloxy)carbonyl]aMino]-1,2,3,6,7,8,9,10,11,13a,14,15,16,16a-tetradecahydro-5,16-dioxo-, Methyl ester, (2S,6S,12Z,13aS,14aR,16aS)-;(2S,6S,12Z,13aS,14aR,16aS)-2-[[(4-Bromophenyl)sulfonyl]oxy]-6-[[(cyclopentyloxy)carbonyl]amino]-1,2,3,6,7,8,9,10,11,13a,14,15,16,16a-tetradecahydro-5,16-dioxo-cyclopropa[e]pyrrolo[1,2-a][1,4]diazacyclopentadecine-14a(5H)-carboxylic acid methyl ester

Chemical Property of Cyclopropa[e]pyrrolo[1,2-a][1,4]diazacyclopentadecine-14a(5H)-carboxylic acid, 2-[[(4-broMophenyl)sulfonyl]oxy]-6-[[(cyclopentyloxy)carbonyl]aMino]-1,2,3,6,7,8,9,10,11,13a,14,15,16,16a-tetradecahydro-5,16-dioxo-, Methyl ester, (2S,6S,12Z,13aS,14aR,16aS)-

Chemical Property:

• PSA: 165.79000
• Density: 1.49±0.1 g/cm3 (20 ºC 760 Torr)
• LogP: 5.46790

Purity/Quality:

97% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Cyclopropa[e]pyrrolo[1,2-a][1,4]diazacyclopentadecine-14a(5H)-carboxylic acid, 2-[[(4-broMophenyl)sulfonyl]oxy]-6-[[(cyclopentyloxy)carbonyl]aMino]-1,2,3,6,7,8,9,10,11,13a,14,15,16,16a-tetradecahydro-5,16-dioxo-, Methyl ester, (2S,6S,12Z,13aS,14aR,16aS)-

There total 15 articles about Cyclopropa[e]pyrrolo[1,2-a][1,4]diazacyclopentadecine-14a(5H)-carboxylic acid, 2-[[(4-broMophenyl)sulfonyl]oxy]-6-[[(cyclopentyloxy)carbonyl]aMino]-1,2,3,6,7,8,9,10,11,13a,14,15,16,16a-tetradecahydro-5,16-dioxo-, Methyl ester, (2S,6S,12Z,13aS,14aR,16aS)- 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:

(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid (13726-69-7,946610-68-0) → (1S,4R,6S,7Z,14S,18S)-18-(4-bromo-benzenesulfonyloxy)-14-cyclopentyloxycarbonylamino-2,15-dioxo-3,16-diaza-tricyclo[14.3.0.04,6]nonadec-7-ene-4-carboxylic acid methyl ester (782479-05-4)

Guidance literature:

Multi-step reaction with 7 steps

1: ethyldiisopropylamine; HOBt; EDC / acetonitrile / 1 h / 22 °C

2: triphenylphosphine; diisopropyl azodicarboxylate / tetrahydrofuran / 2 h / 20 °C

3: 19.4 g / HCl / dioxane / 1 h / 20 °C

4: ethyldiisopropylamine; TBTU / CH₂Cl₂ / 1.5 h / 20 °C

5: Hoveyda catalyst / CH₂Cl₂ / 24 h / 40 °C

6: lithium hydroxide / tetrahydrofuran; H₂O / 3 h / -5 - 0 °C

7: triethylamine; DMAP / CH₂Cl₂; toluene / 15 h / 20 °C

With hydrogenchloride; dmap; lithium hydroxide; di-isopropyl azodicarboxylate; benzotriazol-1-ol; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; dichloro(o-isporopoxyphenylmethylene)(triphenylphosphine)ruthenium(II); In tetrahydrofuran; 1,4-dioxane; dichloromethane; water; toluene; acetonitrile; 2: Mitsunobu reaction;

DOI:10.1021/jo060285j

Reference yield:

(1S,2R)-1-{[(2S,4S)-4-(4-bromo-benzenesulfonyloxy)-1-((S)-2-cyclopentyloxycarbonylamino-oct-7-enoyl)pyrrolidine-2-carbonyl]-amino}-2-vinylcyclopropanecarboxylic acid methyl ester (769167-58-0) → (1S,4R,6S,7Z,14S,18S)-18-(4-bromo-benzenesulfonyloxy)-14-cyclopentyloxycarbonylamino-2,15-dioxo-3,16-diaza-tricyclo[14.3.0.04,6]nonadec-7-ene-4-carboxylic acid methyl ester (782479-05-4)

Guidance literature:

With 3-carboxy-2-mercaptopyridine; dichloro(o-isporopoxyphenylmethylene)(triphenylphosphine)ruthenium(II); In toluene; at 80 ℃; for 20h;

DOI:10.1021/jo060285j

Reference yield:

(S)-2-cyclopentyloxycarbonyl-amino-8-nonenoic acid (769167-55-7) → (1S,4R,6S,7Z,14S,18S)-18-(4-bromo-benzenesulfonyloxy)-14-cyclopentyloxycarbonylamino-2,15-dioxo-3,16-diaza-tricyclo[14.3.0.04,6]nonadec-7-ene-4-carboxylic acid methyl ester (782479-05-4)

Guidance literature:

Multi-step reaction with 4 steps

1: ethyldiisopropylamine; TBTU / CH₂Cl₂ / 1.5 h / 20 °C

2: Hoveyda catalyst / CH₂Cl₂ / 24 h / 40 °C

3: lithium hydroxide / tetrahydrofuran; H₂O / 3 h / -5 - 0 °C

4: triethylamine; DMAP / CH₂Cl₂; toluene / 15 h / 20 °C

With dmap; lithium hydroxide; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; triethylamine; N-ethyl-N,N-diisopropylamine; dichloro(o-isporopoxyphenylmethylene)(triphenylphosphine)ruthenium(II); In tetrahydrofuran; dichloromethane; water; toluene;

DOI:10.1021/jo060285j

upstream raw materials:

(1S,2R)-1-{[(2S,4S)-4-(4-bromo-benzenesulfonyloxy)-1-((S)-2-cyclopentyloxycarbonylamino-oct-7-enoyl)pyrrolidine-2-carbonyl]-amino}-2-vinylcyclopropanecarboxylic acid methyl ester

4-bromobenzenesulfonyl chloride

(1S,4R,6S,7Z,14S,18S)-14-cyclopentyloxycarbonylamino-18-hydroxy-2,15-dioxo-3,16-diaza-tricyclo[14.3.0.0^4,6]nonadec-7-ene-4-carboxylic acid methyl ester

(1R,2S)-1-amino-2-vinylcyclopropane carboxylic acid methyl ester tosylate salt

Downstream raw materials:

ciluprevir