Telaprevir supplier | CasNO.402957-28-2

Name
Cyclopenta(c)pyrrole-1-carboxamide, (2S)-2-cyclohexyl-N-(pyrazinylcarbonyl)glycyl-3-methyl-L-valyl-N-((1S)-1-((cyclopropylamino)oxoacetyl)butyl)octahydro-, (1S,3aR,6aS)-
EINECS 609-814-6
CAS No. 402957-28-2
Article Data12
CAS DataBase
Density 1.25 g/cm³
Solubility
Melting Point
Formula C₃₆H₅₃N₇O₆
Boiling Point
Molecular Weight 679.86
Flash Point
Transport Information
Appearance White powder
Safety 24/25
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms Cyclopenta[c]pyrrole-1-carboxamide,(2S)-2-cyclohexyl-N-(pyrazinylcarbonyl)glycyl-3-methyl-L-valyl-N-[(1S)-1-[(cyclopropylamino)oxoacetyl]butyl]octahydro-,(1S,3aR,6aS)- (9CI);LY 570310;MP 424;VRT 111950;VX 950;
PSA 179.56000
LogP 3.94740

Synthetic route

: (1S,3aR,6aS)-2-[(2S)-2-[[(2S)-2-cyclohexyl-2-[(2-pyrazinylcarbonyl)amino] acetyl]amino]-3,3-dimethylbutanoyl]-N-[(1S)-1-[(cyclopropylamino)(hydroxy)acetyl]butyl]-3,3a,4,5,6,6a-hexahydro-1H-cyclopenta[c]pyrrole-3-carboxamide

: 402957-28-2
(1S,3aR,6aS)-2-((S)-2-((S)-2-cyclohexyl-2-(pyrazine-2-carboxamido)acetamido)-3,3-dimethylbutanoyl)-N-((S)-1-(cyclopropylamino)-1,2-dioxohexan-3-yl)octahydrocyclopenta[c]pyrrole-1-carboxamide

Conditions

Conditions	Yield
With Dess-Martin periodane In dichloromethane at 0 - 5℃; for 2h;	93.61%
With sodium hypochlorite; sodium hydrogencarbonate; sodium bromide In dichloromethane; water at 0 - 5℃;	90%
With sodium hypochlorite; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; sodium hydrogencarbonate In dichloromethane; water at 0 - 25℃; for 3 - 4h; Product distribution / selectivity;	85%

: 1257874-86-4
C38H57N7O7

: 402957-28-2
(1S,3aR,6aS)-2-((S)-2-((S)-2-cyclohexyl-2-(pyrazine-2-carboxamido)acetamido)-3,3-dimethylbutanoyl)-N-((S)-1-(cyclopropylamino)-1,2-dioxohexan-3-yl)octahydrocyclopenta[c]pyrrole-1-carboxamide

Conditions

Conditions	Yield
Stage #1: C38H57N7O7 With methanol; potassium carbonate at 20℃; for 0.5h; Stage #2: With Dess-Martin periodane In dichloromethane at 20℃;	80%
Stage #1: C38H57N7O7 With potassium carbonate In methanol Stage #2: With Dess-Martin periodane In dichloromethane	80%

: (1S,3aR,6aS)-N-((S)-3-deutero-1-(cyclopropylamino)-2-hydroxy-1-oxohexan-3-yl)-2-((S)-2-((S)-2-cyclohexyl-2-(pyrazine-2-carboxamido)acetamido)-3,3-dimethylbutanoyl)octahydrocyclopenta[c]pyrrole-1-carboxamide

A: 402957-28-2
(1S,3aR,6aS)-2-((S)-2-((S)-2-cyclohexyl-2-(pyrazine-2-carboxamido)acetamido)-3,3-dimethylbutanoyl)-N-((S)-1-(cyclopropylamino)-1,2-dioxohexan-3-yl)octahydrocyclopenta[c]pyrrole-1-carboxamide

B: [2H]-Telaprevir

Conditions

Conditions	Yield
With Dess-Martin periodane In dichloromethane at 20℃; for 2h;	A n/a B n/a

: [2H]-Telaprevir

: 402957-28-2
(1S,3aR,6aS)-2-((S)-2-((S)-2-cyclohexyl-2-(pyrazine-2-carboxamido)acetamido)-3,3-dimethylbutanoyl)-N-((S)-1-(cyclopropylamino)-1,2-dioxohexan-3-yl)octahydrocyclopenta[c]pyrrole-1-carboxamide

: 98-97-5
2-pyrazylcarboxylic acid

: 402957-28-2
(1S,3aR,6aS)-2-((S)-2-((S)-2-cyclohexyl-2-(pyrazine-2-carboxamido)acetamido)-3,3-dimethylbutanoyl)-N-((S)-1-(cyclopropylamino)-1,2-dioxohexan-3-yl)octahydrocyclopenta[c]pyrrole-1-carboxamide

Conditions

Conditions	Yield
Multi-step reaction with 6 steps 1.1: (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; triethylamine / dichloromethane / 48 h / 20 °C / Inert atmosphere 2.1: sodium hydroxide / tetrahydrofuran; methanol / 0 - 20 °C 2.2: pH 3.5 3.1: 1-hydroxy-7-aza-benzotriazole; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide / 72 h 4.1: sodium hydroxide / tetrahydrofuran; methanol / 0 - 20 °C 4.2: pH 3.5 5.1: dichloromethane / 72 h / 20 °C 6.1: potassium carbonate; methanol / 0.5 h / 20 °C 6.2: 20 °C View Scheme

Yield

Multi-step reaction with 6 steps
1.1: (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; triethylamine / dichloromethane / 48 h / 20 °C / Inert atmosphere
2.1: sodium hydroxide / tetrahydrofuran; methanol / 0 - 20 °C
2.2: pH 3.5
3.1: 1-hydroxy-7-aza-benzotriazole; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide / 72 h
4.1: sodium hydroxide / tetrahydrofuran; methanol / 0 - 20 °C
4.2: pH 3.5
5.1: dichloromethane / 72 h / 20 °C
6.1: potassium carbonate; methanol / 0.5 h / 20 °C
6.2: 20 °C
View Scheme

: 22724-81-8
L-norvalinol

: 402957-28-2
(1S,3aR,6aS)-2-((S)-2-((S)-2-cyclohexyl-2-(pyrazine-2-carboxamido)acetamido)-3,3-dimethylbutanoyl)-N-((S)-1-(cyclopropylamino)-1,2-dioxohexan-3-yl)octahydrocyclopenta[c]pyrrole-1-carboxamide

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1.1: 20 - 80 °C 1.2: 1 h 1.3: DOWEX50wx8 / pH 7 2.1: Dess-Martin periodane / dichloromethane / 1 h / 20 °C 2.2: 48 h 3.1: bis(trichloromethyl) carbonate; 4-methyl-morpholine / dichloromethane / 3.08 h / -78 - -30 °C 4.1: dichloromethane / 72 h / 20 °C 5.1: potassium carbonate; methanol / 0.5 h / 20 °C 5.2: 20 °C View Scheme

: 145618-11-7
(S)-amino(cyclohexyl)acetic acid methyl ester

: 402957-28-2
(1S,3aR,6aS)-2-((S)-2-((S)-2-cyclohexyl-2-(pyrazine-2-carboxamido)acetamido)-3,3-dimethylbutanoyl)-N-((S)-1-(cyclopropylamino)-1,2-dioxohexan-3-yl)octahydrocyclopenta[c]pyrrole-1-carboxamide

Conditions

Conditions	Yield
Multi-step reaction with 6 steps 1.1: (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; triethylamine / dichloromethane / 48 h / 20 °C / Inert atmosphere 2.1: sodium hydroxide / tetrahydrofuran; methanol / 0 - 20 °C 2.2: pH 3.5 3.1: 1-hydroxy-7-aza-benzotriazole; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide / 72 h 4.1: sodium hydroxide / tetrahydrofuran; methanol / 0 - 20 °C 4.2: pH 3.5 5.1: dichloromethane / 72 h / 20 °C 6.1: potassium carbonate; methanol / 0.5 h / 20 °C 6.2: 20 °C View Scheme

Yield

: 848777-30-0
(2S)-cyclohexyl[(pyrazin-2-ylcarbonyl)amino]ethanoic acid

: 402957-28-2
(1S,3aR,6aS)-2-((S)-2-((S)-2-cyclohexyl-2-(pyrazine-2-carboxamido)acetamido)-3,3-dimethylbutanoyl)-N-((S)-1-(cyclopropylamino)-1,2-dioxohexan-3-yl)octahydrocyclopenta[c]pyrrole-1-carboxamide

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1.1: 1-hydroxy-7-aza-benzotriazole; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide / 72 h 2.1: sodium hydroxide / tetrahydrofuran; methanol / 0 - 20 °C 2.2: pH 3.5 3.1: dichloromethane / 72 h / 20 °C 4.1: potassium carbonate; methanol / 0.5 h / 20 °C 4.2: 20 °C View Scheme

: 848777-29-7
(S)-methyl 2-cyclohexyl-2-(pyrazine-2-carboxamido)acetate

: 402957-28-2
(1S,3aR,6aS)-2-((S)-2-((S)-2-cyclohexyl-2-(pyrazine-2-carboxamido)acetamido)-3,3-dimethylbutanoyl)-N-((S)-1-(cyclopropylamino)-1,2-dioxohexan-3-yl)octahydrocyclopenta[c]pyrrole-1-carboxamide

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1.1: sodium hydroxide / tetrahydrofuran; methanol / 0 - 20 °C 1.2: pH 3.5 2.1: 1-hydroxy-7-aza-benzotriazole; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide / 72 h 3.1: sodium hydroxide / tetrahydrofuran; methanol / 0 - 20 °C 3.2: pH 3.5 4.1: dichloromethane / 72 h / 20 °C 5.1: potassium carbonate; methanol / 0.5 h / 20 °C 5.2: 20 °C View Scheme

Yield

Multi-step reaction with 5 steps
1.1: sodium hydroxide / tetrahydrofuran; methanol / 0 - 20 °C
1.2: pH 3.5
2.1: 1-hydroxy-7-aza-benzotriazole; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide / 72 h
3.1: sodium hydroxide / tetrahydrofuran; methanol / 0 - 20 °C
3.2: pH 3.5
4.1: dichloromethane / 72 h / 20 °C
5.1: potassium carbonate; methanol / 0.5 h / 20 °C
5.2: 20 °C
View Scheme

: 402958-95-6
(S)-methyl 2-((S)-2-cyclohexyl-2-(pyrazine-2-carboxamido)acetamido)-3,3-dimethylbutanoate

: 402957-28-2
(1S,3aR,6aS)-2-((S)-2-((S)-2-cyclohexyl-2-(pyrazine-2-carboxamido)acetamido)-3,3-dimethylbutanoyl)-N-((S)-1-(cyclopropylamino)-1,2-dioxohexan-3-yl)octahydrocyclopenta[c]pyrrole-1-carboxamide

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: sodium hydroxide / tetrahydrofuran; methanol / 0 - 20 °C 1.2: pH 3.5 2.1: dichloromethane / 72 h / 20 °C 3.1: potassium carbonate; methanol / 0.5 h / 20 °C 3.2: 20 °C View Scheme

: 1257874-84-2
(S)-N-(1-hydroxypentan-2-yl)formamide

: 402957-28-2
(1S,3aR,6aS)-2-((S)-2-((S)-2-cyclohexyl-2-(pyrazine-2-carboxamido)acetamido)-3,3-dimethylbutanoyl)-N-((S)-1-(cyclopropylamino)-1,2-dioxohexan-3-yl)octahydrocyclopenta[c]pyrrole-1-carboxamide

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1.1: Dess-Martin periodane / dichloromethane / 1 h / 20 °C 1.2: 48 h 2.1: bis(trichloromethyl) carbonate; 4-methyl-morpholine / dichloromethane / 3.08 h / -78 - -30 °C 3.1: dichloromethane / 72 h / 20 °C 4.1: potassium carbonate; methanol / 0.5 h / 20 °C 4.2: 20 °C View Scheme

: 1257874-85-3
(S)-1-(cyclopropylamino)-3-formamido-1-oxohexan-2-yl acetate

: 402957-28-2
(1S,3aR,6aS)-2-((S)-2-((S)-2-cyclohexyl-2-(pyrazine-2-carboxamido)acetamido)-3,3-dimethylbutanoyl)-N-((S)-1-(cyclopropylamino)-1,2-dioxohexan-3-yl)octahydrocyclopenta[c]pyrrole-1-carboxamide

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: bis(trichloromethyl) carbonate; 4-methyl-morpholine / dichloromethane / 3.08 h / -78 - -30 °C 2.1: dichloromethane / 72 h / 20 °C 3.1: potassium carbonate; methanol / 0.5 h / 20 °C 3.2: 20 °C View Scheme

: 402958-25-2
(1S,3aR,6aS)-ethyl octahydrocyclopenta[c]pyrrole-1-carboxylate

: 402957-28-2
(1S,3aR,6aS)-2-((S)-2-((S)-2-cyclohexyl-2-(pyrazine-2-carboxamido)acetamido)-3,3-dimethylbutanoyl)-N-((S)-1-(cyclopropylamino)-1,2-dioxohexan-3-yl)octahydrocyclopenta[c]pyrrole-1-carboxamide

Conditions

Yield

Multi-step reaction with 4 steps
1: benzotriazol-1-ol; diisopropyl-carbodiimide; copper dichloride / N,N-dimethyl-formamide / 5 h / 0 - 20 °C
2: sodium hydroxide; water / tetrahydrofuran / 18 h / 20 °C
3: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine / dichloromethane / 6 h / 20 °C / Cooling with ice
4: sodium hydrogencarbonate; potassium bromide; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; sodium hypochlorite / dichloromethane / 20 h / 20 °C / Cooling with ice
View Scheme

Multi-step reaction with 4 steps
1: copper dichloride; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide / 22 h / 0 - 20 °C
2: sodium hydroxide; water / tetrahydrofuran / 18 h / 20 °C
3: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine / dichloromethane / 6 h / 20 °C / Cooling with ice
4: sodium hydrogencarbonate; potassium bromide; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; sodium hypochlorite / dichloromethane / 20 h / 20 °C / Cooling with ice
View Scheme

: 1147103-42-1
(1S,3aR,6aS)-ethyl octahydrocyclopenta[c]pyrrole-1-carboxylate hydrochloride

: 402957-28-2
(1S,3aR,6aS)-2-((S)-2-((S)-2-cyclohexyl-2-(pyrazine-2-carboxamido)acetamido)-3,3-dimethylbutanoyl)-N-((S)-1-(cyclopropylamino)-1,2-dioxohexan-3-yl)octahydrocyclopenta[c]pyrrole-1-carboxamide

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: diisopropyl-carbodiimide; 4-methyl-morpholine; copper dichloride / N,N-dimethyl-formamide / 5 h / 20 °C 2: sodium hydroxide; water / tetrahydrofuran / 18 h / 20 °C 3: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine / dichloromethane / 6 h / 20 °C / Cooling with ice 4: sodium hydrogencarbonate; potassium bromide; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; sodium hypochlorite / dichloromethane / 20 h / 20 °C / Cooling with ice View Scheme

Yield

Multi-step reaction with 4 steps
1: diisopropyl-carbodiimide; 4-methyl-morpholine; copper dichloride / N,N-dimethyl-formamide / 5 h / 20 °C
2: sodium hydroxide; water / tetrahydrofuran / 18 h / 20 °C
3: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine / dichloromethane / 6 h / 20 °C / Cooling with ice
4: sodium hydrogencarbonate; potassium bromide; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; sodium hypochlorite / dichloromethane / 20 h / 20 °C / Cooling with ice
View Scheme

: 402958-96-7
(S)-2-((S)-2-cyclohexyl-2-(pyrazine-2-carboxamido)acetamido)-3,3-dimethylbutanoic acid

: 402957-28-2
(1S,3aR,6aS)-2-((S)-2-((S)-2-cyclohexyl-2-(pyrazine-2-carboxamido)acetamido)-3,3-dimethylbutanoyl)-N-((S)-1-(cyclopropylamino)-1,2-dioxohexan-3-yl)octahydrocyclopenta[c]pyrrole-1-carboxamide

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: benzotriazol-1-ol; diisopropyl-carbodiimide; copper dichloride / N,N-dimethyl-formamide / 5 h / 0 - 20 °C 2: sodium hydroxide; water / tetrahydrofuran / 18 h / 20 °C 3: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine / dichloromethane / 6 h / 20 °C / Cooling with ice 4: sodium hydrogencarbonate; potassium bromide; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; sodium hypochlorite / dichloromethane / 20 h / 20 °C / Cooling with ice View Scheme
Multi-step reaction with 4 steps 1: copper dichloride; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide / 22 h / 0 - 20 °C 2: sodium hydroxide; water / tetrahydrofuran / 18 h / 20 °C 3: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine / dichloromethane / 6 h / 20 °C / Cooling with ice 4: sodium hydrogencarbonate; potassium bromide; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; sodium hypochlorite / dichloromethane / 20 h / 20 °C / Cooling with ice View Scheme
Multi-step reaction with 4 steps 1: diisopropyl-carbodiimide; 4-methyl-morpholine; copper dichloride / N,N-dimethyl-formamide / 5 h / 20 °C 2: sodium hydroxide; water / tetrahydrofuran / 18 h / 20 °C 3: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine / dichloromethane / 6 h / 20 °C / Cooling with ice 4: sodium hydrogencarbonate; potassium bromide; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; sodium hypochlorite / dichloromethane / 20 h / 20 °C / Cooling with ice View Scheme

: 402958-97-8
(1S,3aR,6aS)-ethyl 2-((S)-2-((S)-2-cyclohexyl-2-(pyrazine-2-carboxamido)acetamido)-3,3-dimethylbutanoyl)octahydrocyclopenta[c]pyrrole-1-carboxylate

: 402957-28-2
(1S,3aR,6aS)-2-((S)-2-((S)-2-cyclohexyl-2-(pyrazine-2-carboxamido)acetamido)-3,3-dimethylbutanoyl)-N-((S)-1-(cyclopropylamino)-1,2-dioxohexan-3-yl)octahydrocyclopenta[c]pyrrole-1-carboxamide

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: sodium hydroxide; water / tetrahydrofuran / 18 h / 20 °C 2: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine / dichloromethane / 6 h / 20 °C / Cooling with ice 3: sodium hydrogencarbonate; potassium bromide; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; sodium hypochlorite / dichloromethane / 20 h / 20 °C / Cooling with ice View Scheme

Yield

Multi-step reaction with 3 steps
1: sodium hydroxide; water / tetrahydrofuran / 18 h / 20 °C
2: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine / dichloromethane / 6 h / 20 °C / Cooling with ice
3: sodium hydrogencarbonate; potassium bromide; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; sodium hypochlorite / dichloromethane / 20 h / 20 °C / Cooling with ice
View Scheme

: 402960-19-4
3-(S)-3-amino-N-cyclopropyl-2-hydroxyhexanamide

: 402958-98-9
(1S,3aR,6aS)-2-((S)-2-((S)-2-cyclohexyl-2-(pyrazine-2-carboxamido)acetamido)-3,3-dimethylbutanoyl)octahydrocyclopenta[c]pyrrole-1-carboxylic acid

: 402957-28-2
(1S,3aR,6aS)-2-((S)-2-((S)-2-cyclohexyl-2-(pyrazine-2-carboxamido)acetamido)-3,3-dimethylbutanoyl)-N-((S)-1-(cyclopropylamino)-1,2-dioxohexan-3-yl)octahydrocyclopenta[c]pyrrole-1-carboxamide

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine / dichloromethane / 6 h / 20 °C / Cooling with ice 2: sodium hydrogencarbonate; potassium bromide; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; sodium hypochlorite / dichloromethane / 20 h / 20 °C / Cooling with ice View Scheme

: (1S,3aR,6aS)-ethyl 2-(2-((S)-2-cyclohexyl-2-(pyrazine-2-carboxamido)acetamido)-3,3-dimethylbutanoyl)octahydrocyclopenta[c]pyrrole-1-carboxylate

: 402957-28-2
(1S,3aR,6aS)-2-((S)-2-((S)-2-cyclohexyl-2-(pyrazine-2-carboxamido)acetamido)-3,3-dimethylbutanoyl)-N-((S)-1-(cyclopropylamino)-1,2-dioxohexan-3-yl)octahydrocyclopenta[c]pyrrole-1-carboxamide

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: sodium hydroxide; water / ethanol / 20 °C 2: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine / dichloromethane / 6 h / 20 °C / Cooling with ice 3: sodium hydrogencarbonate; potassium bromide; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; sodium hypochlorite / dichloromethane / 20 h / 20 °C / Cooling with ice View Scheme

Yield

Multi-step reaction with 3 steps
1: sodium hydroxide; water / ethanol / 20 °C
2: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine / dichloromethane / 6 h / 20 °C / Cooling with ice
3: sodium hydrogencarbonate; potassium bromide; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; sodium hypochlorite / dichloromethane / 20 h / 20 °C / Cooling with ice
View Scheme

: (S)-ethyl 2,2-diethoxy-3-(((S)-1-phenylethyl)amino)hexanoate

: 402957-28-2
(1S,3aR,6aS)-2-((S)-2-((S)-2-cyclohexyl-2-(pyrazine-2-carboxamido)acetamido)-3,3-dimethylbutanoyl)-N-((S)-1-(cyclopropylamino)-1,2-dioxohexan-3-yl)octahydrocyclopenta[c]pyrrole-1-carboxamide

Conditions

Conditions	Yield
Multi-step reaction with 6 steps 1: palladium 10% on activated carbon; hydrogen / ethanol / 23 h / 20 - 25 °C 2: potassium hydroxide; water / ethanol / 23 h / 20 - 25 °C 3: benzotriazol-1-ol; diisopropyl-carbodiimide / N,N-dimethyl-formamide / 24 h / 20 - 25 °C / Inert atmosphere 4: trifluoroacetic acid / dichloromethane / 18 h / 20 - 25 °C 5: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine / N,N-dimethyl-formamide 6: water; trifluoroacetic acid / acetone / 22 h View Scheme
Multi-step reaction with 6 steps 1: palladium 10% on activated carbon; hydrogen / ethanol / 23 h / 20 °C / Inert atmosphere 2: potassium hydroxide / ethanol; water / 23 h / 20 °C 3: benzotriazol-1-ol; diisopropyl-carbodiimide / N,N-dimethyl-d6-formamide / 24 h / 20 °C / Inert atmosphere 4: trifluoroacetic acid / dichloromethane / 18 h / 20 °C 5: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 15 h / 20 °C 6: sulfuric acid / water; acetone / 17 h / 20 °C View Scheme

Yield

Multi-step reaction with 6 steps
1: palladium 10% on activated carbon; hydrogen / ethanol / 23 h / 20 - 25 °C
2: potassium hydroxide; water / ethanol / 23 h / 20 - 25 °C
3: benzotriazol-1-ol; diisopropyl-carbodiimide / N,N-dimethyl-formamide / 24 h / 20 - 25 °C / Inert atmosphere
4: trifluoroacetic acid / dichloromethane / 18 h / 20 - 25 °C
5: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine / N,N-dimethyl-formamide
6: water; trifluoroacetic acid / acetone / 22 h
View Scheme

Multi-step reaction with 6 steps
1: palladium 10% on activated carbon; hydrogen / ethanol / 23 h / 20 °C / Inert atmosphere
2: potassium hydroxide / ethanol; water / 23 h / 20 °C
3: benzotriazol-1-ol; diisopropyl-carbodiimide / N,N-dimethyl-d6-formamide / 24 h / 20 °C / Inert atmosphere
4: trifluoroacetic acid / dichloromethane / 18 h / 20 °C
5: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 15 h / 20 °C
6: sulfuric acid / water; acetone / 17 h / 20 °C
View Scheme

: (S)-ethyl 3-(((benzyloxy)carbonyl)amino)-2,2-diethoxyhexanoate

: 402957-28-2
(1S,3aR,6aS)-2-((S)-2-((S)-2-cyclohexyl-2-(pyrazine-2-carboxamido)acetamido)-3,3-dimethylbutanoyl)-N-((S)-1-(cyclopropylamino)-1,2-dioxohexan-3-yl)octahydrocyclopenta[c]pyrrole-1-carboxamide

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1: water; sodium hydroxide / ethanol / 24 h 2: benzotriazol-1-ol; diisopropyl-carbodiimide / N,N-dimethyl-formamide / 40 h 3: palladium 10% on activated carbon; hydrogen / ethyl acetate / 1.5 h 4: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine / N,N-dimethyl-formamide 5: water; trifluoroacetic acid / acetone / 22 h View Scheme

Yield

Multi-step reaction with 5 steps
1: water; sodium hydroxide / ethanol / 24 h
2: benzotriazol-1-ol; diisopropyl-carbodiimide / N,N-dimethyl-formamide / 40 h
3: palladium 10% on activated carbon; hydrogen / ethyl acetate / 1.5 h
4: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine / N,N-dimethyl-formamide
5: water; trifluoroacetic acid / acetone / 22 h
View Scheme

: (S)-3-(((benzyloxy)carbonyl)amino)-2,2-diethoxyhexanoic acid

: 402957-28-2
(1S,3aR,6aS)-2-((S)-2-((S)-2-cyclohexyl-2-(pyrazine-2-carboxamido)acetamido)-3,3-dimethylbutanoyl)-N-((S)-1-(cyclopropylamino)-1,2-dioxohexan-3-yl)octahydrocyclopenta[c]pyrrole-1-carboxamide

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: benzotriazol-1-ol; diisopropyl-carbodiimide / N,N-dimethyl-formamide / 40 h 2: palladium 10% on activated carbon; hydrogen / ethyl acetate / 1.5 h 3: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine / N,N-dimethyl-formamide 4: water; trifluoroacetic acid / acetone / 22 h View Scheme

: (S)-benzyl (1-(cyclopropylamino)-2,2-diethoxy-1-oxohexan-3-yl)carbamate

: 402957-28-2
(1S,3aR,6aS)-2-((S)-2-((S)-2-cyclohexyl-2-(pyrazine-2-carboxamido)acetamido)-3,3-dimethylbutanoyl)-N-((S)-1-(cyclopropylamino)-1,2-dioxohexan-3-yl)octahydrocyclopenta[c]pyrrole-1-carboxamide

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: palladium 10% on activated carbon; hydrogen / ethyl acetate / 1.5 h 2: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine / N,N-dimethyl-formamide 3: water; trifluoroacetic acid / acetone / 22 h View Scheme

: (S)-ethyl 3-amino-2,2-diethoxyhexanoate

: 402957-28-2
(1S,3aR,6aS)-2-((S)-2-((S)-2-cyclohexyl-2-(pyrazine-2-carboxamido)acetamido)-3,3-dimethylbutanoyl)-N-((S)-1-(cyclopropylamino)-1,2-dioxohexan-3-yl)octahydrocyclopenta[c]pyrrole-1-carboxamide

Conditions

Conditions	Yield
Multi-step reaction with 6 steps 1: potassium carbonate / tetrahydrofuran / 20 h / 20 - 25 °C 2: water; sodium hydroxide / ethanol / 24 h 3: benzotriazol-1-ol; diisopropyl-carbodiimide / N,N-dimethyl-formamide / 40 h 4: palladium 10% on activated carbon; hydrogen / ethyl acetate / 1.5 h 5: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine / N,N-dimethyl-formamide 6: water; trifluoroacetic acid / acetone / 22 h View Scheme

Yield

Multi-step reaction with 6 steps
1: potassium carbonate / tetrahydrofuran / 20 h / 20 - 25 °C
2: water; sodium hydroxide / ethanol / 24 h
3: benzotriazol-1-ol; diisopropyl-carbodiimide / N,N-dimethyl-formamide / 40 h
4: palladium 10% on activated carbon; hydrogen / ethyl acetate / 1.5 h
5: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine / N,N-dimethyl-formamide
6: water; trifluoroacetic acid / acetone / 22 h
View Scheme

: (S)-3-amino-N-cyclopropyl-2,2-diethoxyhexanamide

: 402958-98-9
(1S,3aR,6aS)-2-((S)-2-((S)-2-cyclohexyl-2-(pyrazine-2-carboxamido)acetamido)-3,3-dimethylbutanoyl)octahydrocyclopenta[c]pyrrole-1-carboxylic acid

: 402957-28-2
(1S,3aR,6aS)-2-((S)-2-((S)-2-cyclohexyl-2-(pyrazine-2-carboxamido)acetamido)-3,3-dimethylbutanoyl)-N-((S)-1-(cyclopropylamino)-1,2-dioxohexan-3-yl)octahydrocyclopenta[c]pyrrole-1-carboxamide

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine / N,N-dimethyl-formamide 2: water; trifluoroacetic acid / acetone / 22 h View Scheme

: ethyl (S)-3-(tert-butoxycarbonylamino)-2,2-diethoxyhexanoate

: 402957-28-2
(1S,3aR,6aS)-2-((S)-2-((S)-2-cyclohexyl-2-(pyrazine-2-carboxamido)acetamido)-3,3-dimethylbutanoyl)-N-((S)-1-(cyclopropylamino)-1,2-dioxohexan-3-yl)octahydrocyclopenta[c]pyrrole-1-carboxamide

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1: potassium hydroxide; water / ethanol / 23 h / 20 - 25 °C 2: benzotriazol-1-ol; diisopropyl-carbodiimide / N,N-dimethyl-formamide / 24 h / 20 - 25 °C / Inert atmosphere 3: trifluoroacetic acid / dichloromethane / 18 h / 20 - 25 °C 4: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine / N,N-dimethyl-formamide 5: water; trifluoroacetic acid / acetone / 22 h View Scheme
Multi-step reaction with 5 steps 1: potassium hydroxide / ethanol; water / 23 h / 20 °C 2: benzotriazol-1-ol; diisopropyl-carbodiimide / N,N-dimethyl-d6-formamide / 24 h / 20 °C / Inert atmosphere 3: trifluoroacetic acid / dichloromethane / 18 h / 20 °C 4: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 15 h / 20 °C 5: sulfuric acid / water; acetone / 17 h / 20 °C View Scheme

Yield

Multi-step reaction with 5 steps
1: potassium hydroxide; water / ethanol / 23 h / 20 - 25 °C
2: benzotriazol-1-ol; diisopropyl-carbodiimide / N,N-dimethyl-formamide / 24 h / 20 - 25 °C / Inert atmosphere
3: trifluoroacetic acid / dichloromethane / 18 h / 20 - 25 °C
4: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine / N,N-dimethyl-formamide
5: water; trifluoroacetic acid / acetone / 22 h
View Scheme

Multi-step reaction with 5 steps
1: potassium hydroxide / ethanol; water / 23 h / 20 °C
2: benzotriazol-1-ol; diisopropyl-carbodiimide / N,N-dimethyl-d6-formamide / 24 h / 20 °C / Inert atmosphere
3: trifluoroacetic acid / dichloromethane / 18 h / 20 °C
4: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 15 h / 20 °C
5: sulfuric acid / water; acetone / 17 h / 20 °C
View Scheme

: (S)-3-((tert-butoxycarbonyl)amino)-2,2-diethoxyhexanoic acid

: 402957-28-2
(1S,3aR,6aS)-2-((S)-2-((S)-2-cyclohexyl-2-(pyrazine-2-carboxamido)acetamido)-3,3-dimethylbutanoyl)-N-((S)-1-(cyclopropylamino)-1,2-dioxohexan-3-yl)octahydrocyclopenta[c]pyrrole-1-carboxamide

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: benzotriazol-1-ol; diisopropyl-carbodiimide / N,N-dimethyl-formamide / 24 h / 20 - 25 °C / Inert atmosphere 2: trifluoroacetic acid / dichloromethane / 18 h / 20 - 25 °C 3: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine / N,N-dimethyl-formamide 4: water; trifluoroacetic acid / acetone / 22 h View Scheme
Multi-step reaction with 4 steps 1: benzotriazol-1-ol; diisopropyl-carbodiimide / N,N-dimethyl-d6-formamide / 24 h / 20 °C / Inert atmosphere 2: trifluoroacetic acid / dichloromethane / 18 h / 20 °C 3: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 15 h / 20 °C 4: sulfuric acid / water; acetone / 17 h / 20 °C View Scheme

: (S)-tert-butyl (1-(cyclopropylamino)-2,2-diethoxy-1-oxohexan-3-yl)carbamate

: 402957-28-2
(1S,3aR,6aS)-2-((S)-2-((S)-2-cyclohexyl-2-(pyrazine-2-carboxamido)acetamido)-3,3-dimethylbutanoyl)-N-((S)-1-(cyclopropylamino)-1,2-dioxohexan-3-yl)octahydrocyclopenta[c]pyrrole-1-carboxamide

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: trifluoroacetic acid / dichloromethane / 18 h / 20 - 25 °C 2: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine / N,N-dimethyl-formamide 3: water; trifluoroacetic acid / acetone / 22 h View Scheme
Multi-step reaction with 3 steps 1: trifluoroacetic acid / dichloromethane / 18 h / 20 °C 2: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 15 h / 20 °C 3: sulfuric acid / water; acetone / 17 h / 20 °C View Scheme

: (1S,3aR,6aS)-2-((S)-2-((S)-2-cyclohexyl-2-(pyrazine-2-carboxamido)acetamido)-3,3-dimethylbutanoyl)-N-((S)-1-(cyclopropylamino)-1-oxo-2,2-diethoxyhexan-3-yl)octahydrocyclopenta[c]pyrrole-1-carboxamide

: 402957-28-2
(1S,3aR,6aS)-2-((S)-2-((S)-2-cyclohexyl-2-(pyrazine-2-carboxamido)acetamido)-3,3-dimethylbutanoyl)-N-((S)-1-(cyclopropylamino)-1,2-dioxohexan-3-yl)octahydrocyclopenta[c]pyrrole-1-carboxamide

Conditions

Conditions	Yield
With water; trifluoroacetic acid In acetone for 22h; Reagent/catalyst;
With sulfuric acid In water; acetone at 20℃; for 17h;

: (1S,3aR,6aS)-2-[(2S)-2-[[(2S)-2-cyclohexyl-2-[(2-pyrazinylcarbonyl)amino] acetyl]amino]-3,3-dimethylbutanoyl]-N-[(1S)-1-[(cyclopropylamino)(hydroxy)acetyl]butyl]-3,3a,4,5,6,6a-hexahydro-1H-cyclopenta[c]pyrrole-3-carboxamide

A: 402957-28-2
(1S,3aR,6aS)-2-((S)-2-((S)-2-cyclohexyl-2-(pyrazine-2-carboxamido)acetamido)-3,3-dimethylbutanoyl)-N-((S)-1-(cyclopropylamino)-1,2-dioxohexan-3-yl)octahydrocyclopenta[c]pyrrole-1-carboxamide

B: C32H48N6O6

C: C31H46N6O5

Conditions

Conditions	Yield
With sodium hypochlorite; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; sodium hydrogencarbonate; potassium hydroxide In dichloromethane; water for 20.5h;	A 20.3 g B 0.8 g C n/a

...Expand

: 402957-28-2
(1S,3aR,6aS)-2-((S)-2-((S)-2-cyclohexyl-2-(pyrazine-2-carboxamido)acetamido)-3,3-dimethylbutanoyl)-N-((S)-1-(cyclopropylamino)-1,2-dioxohexan-3-yl)octahydrocyclopenta[c]pyrrole-1-carboxamide

: C36H53N7O6

: 402957-28-2
(1S,3aR,6aS)-2-((S)-2-((S)-2-cyclohexyl-2-(pyrazine-2-carboxamido)acetamido)-3,3-dimethylbutanoyl)-N-((S)-1-(cyclopropylamino)-1,2-dioxohexan-3-yl)octahydrocyclopenta[c]pyrrole-1-carboxamide

: VRT-127394

Conditions

Conditions	Yield
In acetonitrile at 37℃; for 72h; pH=9; Kinetics; pH-value; Reagent/catalyst; Solvent; Temperature; aq. buffer;

Telaprevir Chemical Properties

Molecular Structure of Telaprevir (CAS NO.402957-28-2):

IUPAC Name: (1S,3aR,6aS)-2-[(2S)-2-[[(2S)-2-cyclohexyl-2-(pyrazine-2-carbonylamino)acetyl]amino]-3,3-dimethylbutanoyl]-N-[1-(cyclopropylamino)-1,2-dioxohexan-3-yl]-3,3a,4,5,6,6a-hexahydro-1H-cyclopenta[c]pyrrole-1-carboxamide
Empirical Formula: C₃₆H₅₃N₇O₆
Molecular Weight: 679.8493
H bond acceptors: 13
H bond donors: 4
Freely Rotating Bonds: 14
Polar Surface Area: 144.4Å²
Index of Refraction: 1.583
Molar Refractivity: 181.37 cm³
Molar Volume: 542 cm³
Surface Tension: 60.1 dyne/cm
Density: 1.25 g/cm³
Product Categories: Telaprevir intermediates
InChI
InChI=1/C36H53N7O6/c1-5-10-25(29(44)34(48)39-23-15-16-23)40-33(47)28-24-14-9-13-22(24)20-43(28)35(49)30(36(2,3)4)42-32(46)27(21-11-7-6-8-12-21)41-31(45)26-19-37-17-18-38-26/h17-19,21-25,27-28,30H,5-16,20H2,1-4H3,(H,39,48)(H,40,47)(H,41,45)(H,42,46)/t22-,24-,25?,27-,28-,30+/m0/s1
Smiles
C(=O)(N[C@@H](CCC)C(=O)C(NC1CC1)=O)[C@H]1N(C([C@H](C(C)(C)C)NC([C@@H](NC(c2nccnc2)=O)C2CCCCC2)=O)=O)C[C@@H]2CCC[C@H]12

Telaprevir Specification

Telaprevir , with CAS number of 402957-28-2, can be called (1S,3aR,6aS)-(2S)-2-Cyclohexyl-N-(pyrazinylcarbonyl)glycyl-3-methyl-L-valyl-N-((1S)-1-((cyclopropylamino)oxoacetyl)butyl)octahydrocyclopenta[c]pyrrole-1-carboxamide .

Product Name

Cyclopenta(c)pyrrole-1-carboxamide, (2S)-2-cyclohexyl-N-(pyrazinylcarbonyl)glycyl-3-methyl-L-valyl-N-((1S)-1-((cyclopropylamino)oxoacetyl)butyl)octahydro-, (1S,3aR,6aS)-

Synthetic route

Telaprevir Chemical Properties

Telaprevir Specification

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