(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

Base Information

Chemical Name:(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
CAS No.:1352302-80-7
Molecular Formula:C₇H₈O₃S*C₂₇H₃₄N₄O₈
Molecular Weight:714.794
Hs Code.:

(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

Synonyms:(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

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Chemical Property of (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

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Technology Process of (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

There total 7 articles about (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 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: 90.0%

: 1352302-78-3
(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

: 104-15-4
toluene-4-sulfonic acid

: 1352302-80-7
(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

Guidance literature:: (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; With trifluoroacetic acid; In dichloromethane; at 40 ℃; for 6h; Industry scale;

With dipotassium hydrogenphosphate; In 2-methyltetrahydrofuran; tert-butyl methyl ether; water; Industry scale;

toluene-4-sulfonic acid; In 2-methyltetrahydrofuran; tert-butyl methyl ether; acetonitrile; for 6h; Product distribution / selectivity; Industry scale;

Reference yield:

: 862119-82-2
(2S,4R)-tert-butyl 2-((1R,2S)-1-(ethoxycarbonyl)-2-vinylcyclopropylcarbamoyl)-4-hydroxypyrrolidine-1-carboxylate

: 1352302-80-7
(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

Guidance literature:: Multi-step reaction with 6 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

6.1: trifluoroacetic acid / dichloromethane / 6 h / 40 °C / Industry scale

6.2: Industry scale

6.3: 6 h / Industry scale

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; trifluoroacetic acid; 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; dichloromethane; ethyl acetate; toluene;

Reference yield:

: 922732-11-4
(2S,4R)-2-((1R,2S)-1-ethoxycarbonyl-2-vinylcyclopropylcarbamoyl)-4-(4-nitrobenzoyloxy)-pyrrolidine-1-carboxylic acid tert-butyl ester

: 1352302-80-7
(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

Guidance literature:: Multi-step reaction with 5 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

5.1: trifluoroacetic acid / dichloromethane / 6 h / 40 °C / Industry scale

5.2: Industry scale

5.3: 6 h / Industry scale

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; trifluoroacetic acid; 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; dichloromethane; ethyl acetate; toluene;