(2R,6S,14aR,16aS,Z)-15-tert-butyl 14a-ethyl 6-(tert-butoxycarbonylamino)-2-(4-nitrobenzoyloxy)-5,16-dioxo-2,3,5,6,7,8,9,10,11,13a,14,14a,16,16a-tetradecahydrocyclopropa[e]pyrrolo[1,2-a][1,4]diazacyclopentadecine-14a,15(1H)-dicarboxylate

Base Information

• Chemical Name: (2R,6S,14aR,16aS,Z)-15-tert-butyl 14a-ethyl 6-(tert-butoxycarbonylamino)-2-(4-nitrobenzoyloxy)-5,16-dioxo-2,3,5,6,7,8,9,10,11,13a,14,14a,16,16a-tetradecahydrocyclopropa[e]pyrrolo[1,2-a][1,4]diazacyclopentadecine-14a,15(1H)-dicarboxylate
• CAS No.: 1352302-78-3
• Molecular Formula: C₃₇H₅₀N₄O₁₂
• Molecular Weight: 742.824
• Mol file: 1352302-78-3.mol

Synonyms:(2R,6S,14aR,16aS,Z)-15-tert-butyl 14a-ethyl 6-(tert-butoxycarbonylamino)-2-(4-nitrobenzoyloxy)-5,16-dioxo-2,3,5,6,7,8,9,10,11,13a,14,14a,16,16a-tetradecahydrocyclopropa[e]pyrrolo[1,2-a][1,4]diazacyclopentadecine-14a,15(1H)-dicarboxylate

Chemical Property of (2R,6S,14aR,16aS,Z)-15-tert-butyl 14a-ethyl 6-(tert-butoxycarbonylamino)-2-(4-nitrobenzoyloxy)-5,16-dioxo-2,3,5,6,7,8,9,10,11,13a,14,14a,16,16a-tetradecahydrocyclopropa[e]pyrrolo[1,2-a][1,4]diazacyclopentadecine-14a,15(1H)-dicarboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,6S,14aR,16aS,Z)-15-tert-butyl 14a-ethyl 6-(tert-butoxycarbonylamino)-2-(4-nitrobenzoyloxy)-5,16-dioxo-2,3,5,6,7,8,9,10,11,13a,14,14a,16,16a-tetradecahydrocyclopropa[e]pyrrolo[1,2-a][1,4]diazacyclopentadecine-14a,15(1H)-dicarboxylate

There total 6 articles about (2R,6S,14aR,16aS,Z)-15-tert-butyl 14a-ethyl 6-(tert-butoxycarbonylamino)-2-(4-nitrobenzoyloxy)-5,16-dioxo-2,3,5,6,7,8,9,10,11,13a,14,14a,16,16a-tetradecahydrocyclopropa[e]pyrrolo[1,2-a][1,4]diazacyclopentadecine-14a,15(1H)-dicarboxylate 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: 93.0%

(3R,5S)-5-(tert-butoxycarbonyl((1R)-1-(ethoxycarbonyl)-2-vinylcyclopropyl)carbamoyl)-1-((S)-2-(tert-butoxycarbonylamino)non-8-enoyl)pyrrolidin-3-yl 4-nitrobenzoate → (2R,6S,14aR,16aS,Z)-15-tert-butyl 14a-ethyl 6-(tert-butoxycarbonylamino)-2-(4-nitrobenzoyloxy)-5,16-dioxo-2,3,5,6,7,8,9,10,11,13a,14,14a,16,16a-tetradecahydrocyclopropa[e]pyrrolo[1,2-a][1,4]diazacyclopentadecine-14a,15(1H)-dicarboxylate (1352302-78-3)

Guidance literature:

(3R,5S)-5-(tert-butoxycarbonyl((1R)-1-(ethoxycarbonyl)-2-vinylcyclopropyl)carbamoyl)-1-((S)-2-(tert-butoxycarbonylamino)non-8-enoyl)pyrrolidin-3-yl 4-nitrobenzoate; 1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidene[2-(iso-propoxy)-5-(N,N-dimethylaminosulfonyl)phenyl]methylene ruthenium(II) dichloride; In toluene; at 60 ℃; for 4h;

With 1H-imidazole; In toluene; at 20 - 60 ℃; Product distribution / selectivity;

Reference yield:

(2S,4R)-tert-butyl 2-((1R,2S)-1-(ethoxycarbonyl)-2-vinylcyclopropylcarbamoyl)-4-hydroxypyrrolidine-1-carboxylate (862119-82-2) → (2R,6S,14aR,16aS,Z)-15-tert-butyl 14a-ethyl 6-(tert-butoxycarbonylamino)-2-(4-nitrobenzoyloxy)-5,16-dioxo-2,3,5,6,7,8,9,10,11,13a,14,14a,16,16a-tetradecahydrocyclopropa[e]pyrrolo[1,2-a][1,4]diazacyclopentadecine-14a,15(1H)-dicarboxylate (1352302-78-3)

Guidance literature:

Multi-step reaction with 5 steps

1.1: dmap; N-ethyl-N,N-diisopropylamine / ethyl acetate / 16 h / 5 - 20 °C

2.1: acetyl chloride; ethanol / ethyl acetate / 18 h / 10 - 20 °C

3.1: N-ethyl-N,N-diisopropylamine; 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide / ethyl acetate; 1-methyl-pyrrolidin-2-one / 14.5 h / 4 - 20 °C

4.1: dmap / toluene / 2 h / 40 °C

5.1: 1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidene[2-(iso-propoxy)-5-(N,N-dimethylaminosulfonyl)phenyl]methylene ruthenium(II) dichloride / toluene / 4 h / 60 °C

5.2: filterol / 20 - 60 °C

With dmap; ethanol; 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; N-ethyl-N,N-diisopropylamine; acetyl chloride; 1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidene[2-(iso-propoxy)-5-(N,N-dimethylaminosulfonyl)phenyl]methylene ruthenium(II) dichloride; In 1-methyl-pyrrolidin-2-one; ethyl acetate; toluene;

Reference yield:

(2S,4R)-2-((1R,2S)-1-ethoxycarbonyl-2-vinylcyclopropylcarbamoyl)-4-(4-nitrobenzoyloxy)-pyrrolidine-1-carboxylic acid tert-butyl ester (922732-11-4) → (2R,6S,14aR,16aS,Z)-15-tert-butyl 14a-ethyl 6-(tert-butoxycarbonylamino)-2-(4-nitrobenzoyloxy)-5,16-dioxo-2,3,5,6,7,8,9,10,11,13a,14,14a,16,16a-tetradecahydrocyclopropa[e]pyrrolo[1,2-a][1,4]diazacyclopentadecine-14a,15(1H)-dicarboxylate (1352302-78-3)

Guidance literature:

Multi-step reaction with 4 steps

1.1: acetyl chloride; ethanol / ethyl acetate / 18 h / 10 - 20 °C

2.1: N-ethyl-N,N-diisopropylamine; 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide / ethyl acetate; 1-methyl-pyrrolidin-2-one / 14.5 h / 4 - 20 °C

3.1: dmap / toluene / 2 h / 40 °C

4.1: 1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidene[2-(iso-propoxy)-5-(N,N-dimethylaminosulfonyl)phenyl]methylene ruthenium(II) dichloride / toluene / 4 h / 60 °C

4.2: filterol / 20 - 60 °C

With dmap; ethanol; 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; N-ethyl-N,N-diisopropylamine; acetyl chloride; 1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidene[2-(iso-propoxy)-5-(N,N-dimethylaminosulfonyl)phenyl]methylene ruthenium(II) dichloride; In 1-methyl-pyrrolidin-2-one; ethyl acetate; toluene;

upstream raw materials:

4-nitro-benzoyl chloride

(2S,4R)-tert-butyl 2-((1R,2S)-1-(ethoxycarbonyl)-2-vinylcyclopropylcarbamoyl)-4-hydroxypyrrolidine-1-carboxylate

(2S,4R)-2-((1R,2S)-1-ethoxycarbonyl-2-vinylcyclopropylcarbamoyl)-4-(4-nitrobenzoyloxy)-pyrrolidine-1-carboxylic acid tert-butyl ester

(2S,4R)-2-((1R,2S)-1-(ethoxycarbonyl)-2-vinylcyclopropylcarbamoyl)-4-(4-nitrobenzoyloxy)pyrrolidinium chloride

Downstream raw materials:

(2R,6S,13aS,14aR,16aS,Z)-14a-(ethoxycarbonyl)-2-(4-nitrobenzoyloxy)-5,16-dioxo-1,2,3,5,6,7,8,9,10,11,13a,14,14a,15,16,16a-hexadecahydrocyclopropa[e]pyrrolo[1,2-a][1,4]diazacyclopentadecin-6-aminium 4-methylbenzenesulfonate

(2R,6S,13aS,14aR,16aS,Z)-ethyl 6-(5-methylisoxazole-3-carboxamido)-2-(4-nitrobenzoyloxy)-5,16-dioxo-1,2,3,5,6,7,8,9,10,11,13a,14,14a,15,16,16a-hexadecahydrocyclopropa[e]pyrrolo[1,2-a][1,4]diazacyclopentadecine-14a-carboxylate

Refernces