N-{1-cyclohexyl-2-[(6R)-(6-fluoro-1H-indol-3-yl)-3-hydroxy-hexahydro-pyrrolo[3,2-b]pyrrol-1-yl]-2-oxo-ethyl}-2-methylamino-propionamide

Base Information

Chemical Name:N-{1-cyclohexyl-2-[(6R)-(6-fluoro-1H-indol-3-yl)-3-hydroxy-hexahydro-pyrrolo[3,2-b]pyrrol-1-yl]-2-oxo-ethyl}-2-methylamino-propionamide
CAS No.:1218930-97-2
Molecular Formula:C₂₆H₃₆FN₅O₃
Molecular Weight:485.602
Hs Code.:

Synonyms:N-{1-cyclohexyl-2-[(6R)-(6-fluoro-1H-indol-3-yl)-3-hydroxy-hexahydro-pyrrolo[3,2-b]pyrrol-1-yl]-2-oxo-ethyl}-2-methylamino-propionamide

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Chemical Property of N-{1-cyclohexyl-2-[(6R)-(6-fluoro-1H-indol-3-yl)-3-hydroxy-hexahydro-pyrrolo[3,2-b]pyrrol-1-yl]-2-oxo-ethyl}-2-methylamino-propionamide

Chemical Property:

Purity/Quality:: 98% ^*data from raw suppliers

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Technology Process of N-{1-cyclohexyl-2-[(6R)-(6-fluoro-1H-indol-3-yl)-3-hydroxy-hexahydro-pyrrolo[3,2-b]pyrrol-1-yl]-2-oxo-ethyl}-2-methylamino-propionamide

There total 20 articles about N-{1-cyclohexyl-2-[(6R)-(6-fluoro-1H-indol-3-yl)-3-hydroxy-hexahydro-pyrrolo[3,2-b]pyrrol-1-yl]-2-oxo-ethyl}-2-methylamino-propionamide 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: 70.0%

: 1218931-17-9
acetic acid 1-[2-cyclohexyl-2-(2-methylamino-propionylamino)-acetyl]-(6R)-(6-fluoro-1H-indol-3-yl)-octahydro-pyrrolo[3,2-b]pyrrol-3-yl ester

: 1218930-97-2
N-{1-cyclohexyl-2-[(6R)-(6-fluoro-1H-indol-3-yl)-3-hydroxy-hexahydro-pyrrolo[3,2-b]pyrrol-1-yl]-2-oxo-ethyl}-2-methylamino-propionamide

Guidance literature:: acetic acid 1-[2-cyclohexyl-2-(2-methylamino-propionylamino)-acetyl]-(6R)-(6-fluoro-1H-indol-3-yl)-octahydro-pyrrolo[3,2-b]pyrrol-3-yl ester; With methanol; sodium hydroxide; for 75h;

With acetic acid; In methanol;

Reference yield:

: 137934-80-6
4-(tert-butyl-dimethyl-silanyloxy)-2-(2-nitro-vinyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

: 1218930-97-2
N-{1-cyclohexyl-2-[(6R)-(6-fluoro-1H-indol-3-yl)-3-hydroxy-hexahydro-pyrrolo[3,2-b]pyrrol-1-yl]-2-oxo-ethyl}-2-methylamino-propionamide

Guidance literature:: Multi-step reaction with 18 steps

1.1: silica gel; sodium iodide / cerium(III) chloride heptahydrate / acetonitrile

1.2: 72 h / 20 °C / Neat (no solvent)

2.1: hydrogen / ethanol; water / 2.5 h / 2585.81 Torr

3.1: triethylamine / dichloromethane / 17 h / 0 - 20 °C

4.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 5 h / 20 °C

5.1: pyridine-SO₃ complex; triethylamine / dichloromethane; dimethyl sulfoxide / 3 h / 0 - 20 °C

6.1: sodium hexamethyldisilazane / tetrahydrofuran / 1 h / -78 °C

6.2: 4.17 h / -78 °C

7.1: borane-THF / tetrahydrofuran / -30 - 20 °C

7.2: 0 - 20 °C

8.1: N-ethyl-N,N-diisopropylamine / dmap / dichloromethane / 2 h / 0 °C

9.1: hydrogen / palladium 10% on activated carbon / methanol / 2.5 h / 2585.81 Torr

9.2: 0.25 h / 80 °C

10.1: triethylamine / dmap / dichloromethane / 0 - 20 °C

11.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 20 °C

12.1: triethylamine / dmap / dichloromethane / 0 - 20 °C

13.1: trifluoroacetic acid / dichloromethane / 2 h / 0 °C

14.1: N-ethyl-N,N-diisopropylamine; HATU / 1-methyl-pyrrolidin-2-one / 0.5 h / 0 °C

14.2: 16 h / 0 - 20 °C

15.1: trifluoroacetic acid / dichloromethane / 2.5 h / 0 °C

16.1: N-ethyl-N,N-diisopropylamine; HATU / 1-methyl-pyrrolidin-2-one / 0.5 h / 0 °C

16.2: 16 h / 0 - 20 °C

17.1: hydrogen / palladium 10% on activated carbon / methanol / 2 h / 2585.81 Torr

18.1: methanol; sodium hydroxide / 75 h

With methanol; borane-THF; pyridine-SO₃ complex; tetrabutyl ammonium fluoride; hydrogen; sodium hexamethyldisilazane; silica gel; triethylamine; N-ethyl-N,N-diisopropylamine; HATU; trifluoroacetic acid; sodium iodide; sodium hydroxide; dmap; cerium(III) chloride heptahydrate; palladium 10% on activated carbon; In tetrahydrofuran; 1-methyl-pyrrolidin-2-one; methanol; ethanol; dichloromethane; water; dimethyl sulfoxide; acetonitrile;

Reference yield:

: 1218930-82-5
2-[2-amino-1-(6-fluoro-1H-indol-3-yl)-ethyl]-4-(tert-butyl-dimethyl-silanyloxy)-pyrrolidine-1-carboxylic acid tert-butyl ester

: 1218930-97-2
N-{1-cyclohexyl-2-[(6R)-(6-fluoro-1H-indol-3-yl)-3-hydroxy-hexahydro-pyrrolo[3,2-b]pyrrol-1-yl]-2-oxo-ethyl}-2-methylamino-propionamide

Guidance literature:: Multi-step reaction with 16 steps

1.1: triethylamine / dichloromethane / 17 h / 0 - 20 °C

2.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 5 h / 20 °C

3.1: pyridine-SO₃ complex; triethylamine / dichloromethane; dimethyl sulfoxide / 3 h / 0 - 20 °C

4.1: sodium hexamethyldisilazane / tetrahydrofuran / 1 h / -78 °C

4.2: 4.17 h / -78 °C

5.1: borane-THF / tetrahydrofuran / -30 - 20 °C

5.2: 0 - 20 °C

6.1: N-ethyl-N,N-diisopropylamine / dmap / dichloromethane / 2 h / 0 °C

7.1: hydrogen / palladium 10% on activated carbon / methanol / 2.5 h / 2585.81 Torr

7.2: 0.25 h / 80 °C

8.1: triethylamine / dmap / dichloromethane / 0 - 20 °C

9.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 20 °C

10.1: triethylamine / dmap / dichloromethane / 0 - 20 °C

11.1: trifluoroacetic acid / dichloromethane / 2 h / 0 °C

12.1: N-ethyl-N,N-diisopropylamine; HATU / 1-methyl-pyrrolidin-2-one / 0.5 h / 0 °C

12.2: 16 h / 0 - 20 °C

13.1: trifluoroacetic acid / dichloromethane / 2.5 h / 0 °C

14.1: N-ethyl-N,N-diisopropylamine; HATU / 1-methyl-pyrrolidin-2-one / 0.5 h / 0 °C

14.2: 16 h / 0 - 20 °C

15.1: hydrogen / palladium 10% on activated carbon / methanol / 2 h / 2585.81 Torr

16.1: methanol; sodium hydroxide / 75 h

With methanol; borane-THF; pyridine-SO₃ complex; tetrabutyl ammonium fluoride; hydrogen; sodium hexamethyldisilazane; triethylamine; N-ethyl-N,N-diisopropylamine; HATU; trifluoroacetic acid; sodium hydroxide; dmap; palladium 10% on activated carbon; In tetrahydrofuran; 1-methyl-pyrrolidin-2-one; methanol; dichloromethane; dimethyl sulfoxide;