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402957-28-2
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Basic Information
CAS No.: 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)-
Molecular Structure:
Molecular Structure of 402957-28-2 (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)-)
Formula: C36H53N7O6
Molecular Weight: 679.86
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;
EINECS: 609-814-6
Density: 1.25 g/cm3
Appearance: White powder
Safety: 24/25
PSA: 179.56000
LogP: 3.94740
Related products
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
Raw Materials
402958-25-2
402960-19-4
402958-95-6
402958-98-9
848777-30-0
848777-29-7
22724-81-8
402958-96-7
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Chemistry

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

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 .

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