Product Name

  • Name

    Des[N-[(1S)-1-[2-(cyclopropylaMino)-2-oxoacetyl]butyl]carboxaMido] 1-Carboxy Telaprevir

  • EINECS
  • CAS No. 402958-98-9
  • Article Data3
  • CAS DataBase
  • Density 1.2±0.1 g/cm3
  • Solubility
  • Melting Point
  • Formula C27H39N5O5
  • Boiling Point 817.7±65.0 °C at 760 mmHg
  • Molecular Weight 513.637
  • Flash Point 448.3±34.3 °C
  • Transport Information
  • Appearance
  • Safety
  • Risk Codes
  • Molecular Structure Molecular Structure of 402958-98-9 (Des[N-[(1S)-1-[2-(cyclopropylaMino)-2-oxoacetyl]butyl]carboxaMido] 1-Carboxy Telaprevir)
  • Hazard Symbols
  • Synonyms (1S,3aR,6aS)-2-((S)-2-((S)-2-cyclohexyl-2-(pyrazine-2-carboxamido)acetamido)-3,3-dimethylbutanoyl)octahydrocyclopenta[c]pyrrole-1-carboxylic acid; Des[N-[(1S)-1-[2-(cyclopropylamino)-2-oxoacetyl]butyl]carboxamido] 1-Carboxy Telaprevir; GUAIOL; Champacol; guai-1(5)-en-11-ol; (1S)-2-((S)-2-((S)-2-cyclohexyl-2-(pyrazine-2-carboxamido)acetamido)-3,3-dimethylbutanoyl)octahydrocyclopenta[c]pyrrole-1-carboxylic acid; cyclopentenoncyanhydrin glycoside gynocardin; Gualol; GUAIOL(RG); Champaca camphor; Champaeol; Guaiac alcohol; 查看更多英文别名 收起
  • PSA 148.57000
  • LogP 3.75090

Synthetic route

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

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

Conditions
ConditionsYield
With sodium hydroxide100%
With water; sodium hydroxide In tetrahydrofuran at 20℃; for 18h; Reagent/catalyst; Temperature; Time;2.82 g
2-pyrazylcarboxylic acid
98-97-5

2-pyrazylcarboxylic acid

piperazine-derivatized ArgoGelTM Wang resin

piperazine-derivatized ArgoGelTM Wang resin

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

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: HOBt; EDCl
2: 100 percent / aq. NaOH / methanol
3: 100 percent / HOAt; DCC / CH2Cl2; tetrahydrofuran
4: 100 percent / aq. NaOH
View Scheme
L-tert-leucine methyl ester hydrochloride
63038-27-7

L-tert-leucine methyl ester hydrochloride

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

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: 30 percent / HOBt; EDCl / tetrahydrofuran
2: HCl / dioxane; tetrahydrofuran
3: HOBt; EDCl
4: 100 percent / aq. NaOH / methanol
5: 100 percent / HOAt; DCC / CH2Cl2; tetrahydrofuran
6: 100 percent / aq. NaOH
View Scheme
N-(tert-butoxycarbonyl)-L-cyclohexylglycine
109183-71-3

N-(tert-butoxycarbonyl)-L-cyclohexylglycine

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

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: 30 percent / HOBt; EDCl / tetrahydrofuran
2: HCl / dioxane; tetrahydrofuran
3: HOBt; EDCl
4: 100 percent / aq. NaOH / methanol
5: 100 percent / HOAt; DCC / CH2Cl2; tetrahydrofuran
6: 100 percent / aq. NaOH
View Scheme
(S)-2-((S)-2-tert-Butoxycarbonylamino-2-cyclohexyl-acetylamino)-3,3-dimethyl-butyric acid methyl ester
402958-93-4

(S)-2-((S)-2-tert-Butoxycarbonylamino-2-cyclohexyl-acetylamino)-3,3-dimethyl-butyric acid methyl ester

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

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: HCl / dioxane; tetrahydrofuran
2: HOBt; EDCl
3: 100 percent / aq. NaOH / methanol
4: 100 percent / HOAt; DCC / CH2Cl2; tetrahydrofuran
5: 100 percent / aq. NaOH
View Scheme
(S)-2-((S)-2-cyclohexyl-2-(pyrazine-2-carboxamido)acetamido)-3,3-dimethylbutanoic acid
402958-96-7

(S)-2-((S)-2-cyclohexyl-2-(pyrazine-2-carboxamido)acetamido)-3,3-dimethylbutanoic acid

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

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 100 percent / HOAt; DCC / CH2Cl2; tetrahydrofuran
2: 100 percent / aq. NaOH
View Scheme
Multi-step reaction with 2 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
View Scheme
Multi-step reaction with 2 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
View Scheme
Multi-step reaction with 2 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
View Scheme
(S)-methyl 2-((S)-2-cyclohexyl-2-(pyrazine-2-carboxamido)acetamido)-3,3-dimethylbutanoate
402958-95-6

(S)-methyl 2-((S)-2-cyclohexyl-2-(pyrazine-2-carboxamido)acetamido)-3,3-dimethylbutanoate

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

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 100 percent / aq. NaOH / methanol
2: 100 percent / HOAt; DCC / CH2Cl2; tetrahydrofuran
3: 100 percent / aq. NaOH
View Scheme
H2N-Chg-(t-Bu)Gly-OMe hydrochloride

H2N-Chg-(t-Bu)Gly-OMe hydrochloride

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

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: HOBt; EDCl
2: 100 percent / aq. NaOH / methanol
3: 100 percent / HOAt; DCC / CH2Cl2; tetrahydrofuran
4: 100 percent / aq. NaOH
View Scheme
(1S,3aR,6aS)-tert-butyl 2-((S)-2-((S)-2-cyclohexyl-2-(pyrazine-2-carboxamido)acetamido)-3,3-dimethylbutanoyl)octahydrocyclopenta[c]pyrrole-1-carboxylate
926276-19-9

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

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

Conditions
ConditionsYield
With hydrogenchloride; water In formic acid at 0℃; for 3.3h; Product distribution / selectivity;
With hydrogenchloride; water In dichloromethane at 0 - 10℃; for 3h; Product distribution / selectivity;
(1S,3aR,6aS)-ethyl octahydrocyclopenta[c]pyrrole-1-carboxylate
402958-25-2

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

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

Conditions
ConditionsYield
Multi-step reaction with 2 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
View Scheme
Multi-step reaction with 2 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
View Scheme
C10H17NO2*ClH
1147103-42-1

C10H17NO2*ClH

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

Conditions
ConditionsYield
Multi-step reaction with 2 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
View Scheme
(1S,3aR,6aS)-ethyl 2-(2-((S)-2-cyclohexyl-2-(pyrazine-2-carboxamido)acetamido)-3,3-dimethylbutanoyl)octahydrocyclopenta[c]pyrrole-1-carboxylate

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

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

Conditions
ConditionsYield
With water; sodium hydroxide In ethanol at 20℃;5.29 g
(S)-3-amino-N-cyclopropyl-2,2-diethoxyhexanamide

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

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

(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

(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

Conditions
ConditionsYield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In N,N-dimethyl-formamide Solvent;96%
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 15h;88%
3-(S)-3-amino-N-cyclopropyl-2-hydroxyhexanamide
402960-19-4

3-(S)-3-amino-N-cyclopropyl-2-hydroxyhexanamide

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

(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

(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

Conditions
ConditionsYield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane at 20℃; for 6h; Cooling with ice;94%
Stage #1: 3-(S)-3-amino-N-cyclopropyl-2-hydroxyhexanamide; (1S,3aR,6aS)-2-((S)-2-((S)-2-cyclohexyl-2-(pyrazine-2-carboxamido)acetamido)-3,3-dimethylbutanoyl)octahydrocyclopenta[c]pyrrole-1-carboxylic acid With 4-methyl-morpholine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane; water at 10 - 20℃; for 4.33h;
Stage #2: With sodium hydrogencarbonate In dichloromethane; water Product distribution / selectivity;
Stage #1: 3-(S)-3-amino-N-cyclopropyl-2-hydroxyhexanamide; (1S,3aR,6aS)-2-((S)-2-((S)-2-cyclohexyl-2-(pyrazine-2-carboxamido)acetamido)-3,3-dimethylbutanoyl)octahydrocyclopenta[c]pyrrole-1-carboxylic acid With 4-methyl-morpholine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane; water at 0 - 20℃; for 5h;
Stage #2: With hydrogenchloride In dichloromethane; water
Stage #3: With sodium hydrogencarbonate In dichloromethane; water Product distribution / selectivity;
3-amino-N-cyclopropyl-2-hydroxylhexanamide
402958-32-1

3-amino-N-cyclopropyl-2-hydroxylhexanamide

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

(1S,3aR,6aS)-2-((S)-2-{(S)-2-Cyclohexyl-2-[(pyrazine-2-carbonyl)-amino]-acetylamino}-3,3-dimethyl-butyryl)-octahydro-cyclopenta[c]pyrrole-1-carboxylic acid [1-(cyclopropylcarbamoyl-hydroxy-methyl)-butyl]-amide
402958-99-0

(1S,3aR,6aS)-2-((S)-2-{(S)-2-Cyclohexyl-2-[(pyrazine-2-carbonyl)-amino]-acetylamino}-3,3-dimethyl-butyryl)-octahydro-cyclopenta[c]pyrrole-1-carboxylic acid [1-(cyclopropylcarbamoyl-hydroxy-methyl)-butyl]-amide

Conditions
ConditionsYield
With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine88%
3-Amino-2-hydroxy-hexanoic acid ((S)-1-phenyl-ethyl)-amide

3-Amino-2-hydroxy-hexanoic acid ((S)-1-phenyl-ethyl)-amide

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

(1S,3aR,6aS)-2-((S)-2-{(S)-2-Cyclohexyl-2-[(pyrazine-2-carbonyl)-amino]-acetylamino}-3,3-dimethyl-butyryl)-octahydro-cyclopenta[c]pyrrole-1-carboxylic acid {1-[hydroxy-((S)-1-phenyl-ethylcarbamoyl)-methyl]-butyl}-amide

(1S,3aR,6aS)-2-((S)-2-{(S)-2-Cyclohexyl-2-[(pyrazine-2-carbonyl)-amino]-acetylamino}-3,3-dimethyl-butyryl)-octahydro-cyclopenta[c]pyrrole-1-carboxylic acid {1-[hydroxy-((S)-1-phenyl-ethylcarbamoyl)-methyl]-butyl}-amide

Conditions
ConditionsYield
With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine
3-amino-2-hydroxy-hexanoic acid sec-butylamide

3-amino-2-hydroxy-hexanoic acid sec-butylamide

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

(1S,3aR,6aS)-2-((S)-2-{(S)-2-Cyclohexyl-2-[(pyrazine-2-carbonyl)-amino]-acetylamino}-3,3-dimethyl-butyryl)-octahydro-cyclopenta[c]pyrrole-1-carboxylic acid {1-[((S)-sec-butylcarbamoyl)-hydroxy-methyl]-butyl}-amide

(1S,3aR,6aS)-2-((S)-2-{(S)-2-Cyclohexyl-2-[(pyrazine-2-carbonyl)-amino]-acetylamino}-3,3-dimethyl-butyryl)-octahydro-cyclopenta[c]pyrrole-1-carboxylic acid {1-[((S)-sec-butylcarbamoyl)-hydroxy-methyl]-butyl}-amide

Conditions
ConditionsYield
With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine
3-amino-5,5-difluoro-2-hydroxy-pentanoic acid cyclopropylamide

3-amino-5,5-difluoro-2-hydroxy-pentanoic acid cyclopropylamide

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

(1S,3aR,6aS)-2-((S)-2-{(S)-2-Cyclohexyl-2-[(pyrazine-2-carbonyl)-amino]-acetylamino}-3,3-dimethyl-butyryl)-octahydro-cyclopenta[c]pyrrole-1-carboxylic acid [1-(cyclopropylcarbamoyl-hydroxy-methyl)-3,3-difluoro-propyl]-amide

(1S,3aR,6aS)-2-((S)-2-{(S)-2-Cyclohexyl-2-[(pyrazine-2-carbonyl)-amino]-acetylamino}-3,3-dimethyl-butyryl)-octahydro-cyclopenta[c]pyrrole-1-carboxylic acid [1-(cyclopropylcarbamoyl-hydroxy-methyl)-3,3-difluoro-propyl]-amide

Conditions
ConditionsYield
With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine
3-Amino-2-hydroxy-hexanoic acid ((S)-1,2-dimethyl-propyl)-amide

3-Amino-2-hydroxy-hexanoic acid ((S)-1,2-dimethyl-propyl)-amide

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

(1S,3aR,6aS)-2-((S)-2-{(S)-2-Cyclohexyl-2-[(pyrazine-2-carbonyl)-amino]-acetylamino}-3,3-dimethyl-butyryl)-octahydro-cyclopenta[c]pyrrole-1-carboxylic acid {1-[((S)-1,2-dimethyl-propylcarbamoyl)-hydroxy-methyl]-butyl}-amide

(1S,3aR,6aS)-2-((S)-2-{(S)-2-Cyclohexyl-2-[(pyrazine-2-carbonyl)-amino]-acetylamino}-3,3-dimethyl-butyryl)-octahydro-cyclopenta[c]pyrrole-1-carboxylic acid {1-[((S)-1,2-dimethyl-propylcarbamoyl)-hydroxy-methyl]-butyl}-amide

Conditions
ConditionsYield
With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine
(1S,3aR,6aS)-2-((S)-2-((S)-2-cyclohexyl-2-(pyrazine-2-carboxamido)acetamido)-3,3-dimethylbutanoyl)octahydrocyclopenta[c]pyrrole-1-carboxylic acid
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

VX-950

VX-950

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 88 percent / PyBOP; i-Pr2NEt
2: 50 percent / Dess-Martin periodinane
View Scheme
(1S,3aR,6aS)-2-((S)-2-((S)-2-cyclohexyl-2-(pyrazine-2-carboxamido)acetamido)-3,3-dimethylbutanoyl)octahydrocyclopenta[c]pyrrole-1-carboxylic acid
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

(1S,3aR,6aS)-2-((S)-2-{(S)-2-Cyclohexyl-2-[(pyrazine-2-carbonyl)-amino]-acetylamino}-3,3-dimethyl-butyryl)-octahydro-cyclopenta[c]pyrrole-1-carboxylic acid (1-cyclopropylaminooxalyl-3,3-difluoro-propyl)-amide

(1S,3aR,6aS)-2-((S)-2-{(S)-2-Cyclohexyl-2-[(pyrazine-2-carbonyl)-amino]-acetylamino}-3,3-dimethyl-butyryl)-octahydro-cyclopenta[c]pyrrole-1-carboxylic acid (1-cyclopropylaminooxalyl-3,3-difluoro-propyl)-amide

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: PyBOP; i-Pr2NEt
2: 50 percent / Dess-Martin periodinane
View Scheme
(1S,3aR,6aS)-2-((S)-2-((S)-2-cyclohexyl-2-(pyrazine-2-carboxamido)acetamido)-3,3-dimethylbutanoyl)octahydrocyclopenta[c]pyrrole-1-carboxylic acid
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

(1S,3aR,6aS)-2-((S)-2-{(S)-2-Cyclohexyl-2-[(pyrazine-2-carbonyl)-amino]-acetylamino}-3,3-dimethyl-butyryl)-octahydro-cyclopenta[c]pyrrole-1-carboxylic acid [1-((S)-1,2-dimethyl-propylaminooxalyl)-butyl]-amide

(1S,3aR,6aS)-2-((S)-2-{(S)-2-Cyclohexyl-2-[(pyrazine-2-carbonyl)-amino]-acetylamino}-3,3-dimethyl-butyryl)-octahydro-cyclopenta[c]pyrrole-1-carboxylic acid [1-((S)-1,2-dimethyl-propylaminooxalyl)-butyl]-amide

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: PyBOP; i-Pr2NEt
2: Dess-Martin periodinane
View Scheme
(1S,3aR,6aS)-2-((S)-2-((S)-2-cyclohexyl-2-(pyrazine-2-carboxamido)acetamido)-3,3-dimethylbutanoyl)octahydrocyclopenta[c]pyrrole-1-carboxylic acid
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

(1S,3aR,6aS)-2-((S)-2-{(S)-2-Cyclohexyl-2-[(pyrazine-2-carbonyl)-amino]-acetylamino}-3,3-dimethyl-butyryl)-octahydro-cyclopenta[c]pyrrole-1-carboxylic acid [1-((S)-sec-butylaminooxalyl)-butyl]-amide

(1S,3aR,6aS)-2-((S)-2-{(S)-2-Cyclohexyl-2-[(pyrazine-2-carbonyl)-amino]-acetylamino}-3,3-dimethyl-butyryl)-octahydro-cyclopenta[c]pyrrole-1-carboxylic acid [1-((S)-sec-butylaminooxalyl)-butyl]-amide

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: PyBOP; i-Pr2NEt
2: Dess-Martin periodinane
View Scheme
(1S,3aR,6aS)-2-((S)-2-((S)-2-cyclohexyl-2-(pyrazine-2-carboxamido)acetamido)-3,3-dimethylbutanoyl)octahydrocyclopenta[c]pyrrole-1-carboxylic acid
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

(1S,3aR,6aS)-2-((S)-2-{(S)-2-Cyclohexyl-2-[(pyrazine-2-carbonyl)-amino]-acetylamino}-3,3-dimethyl-butyryl)-octahydro-cyclopenta[c]pyrrole-1-carboxylic acid [1-((S)-1-phenyl-ethylaminooxalyl)-butyl]-amide

(1S,3aR,6aS)-2-((S)-2-{(S)-2-Cyclohexyl-2-[(pyrazine-2-carbonyl)-amino]-acetylamino}-3,3-dimethyl-butyryl)-octahydro-cyclopenta[c]pyrrole-1-carboxylic acid [1-((S)-1-phenyl-ethylaminooxalyl)-butyl]-amide

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: PyBOP; i-Pr2NEt
2: Dess-Martin periodinane
View Scheme
(3S)-3-amino-N-cyclopropyl-2-hydroxyhexanamide hydrochloride
850252-34-5

(3S)-3-amino-N-cyclopropyl-2-hydroxyhexanamide hydrochloride

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

(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

(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

Conditions
ConditionsYield
Stage #1: (3S)-3-amino-N-cyclopropyl-2-hydroxyhexanamide hydrochloride; (1S,3aR,6aS)-2-((S)-2-((S)-2-cyclohexyl-2-(pyrazine-2-carboxamido)acetamido)-3,3-dimethylbutanoyl)octahydrocyclopenta[c]pyrrole-1-carboxylic acid With 4-methyl-morpholine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane; water at 0 - 25℃; for 6 - 6.5h;
Stage #2: With hydrogenchloride In dichloromethane; water
Stage #3: With sodium hydrogencarbonate In dichloromethane; water Product distribution / selectivity;
(2S,3S)-3-amino-3-deutero-N-cyclopropyl-2-hydroxyhexanamide hydrochloric acid salt
950842-32-7

(2S,3S)-3-amino-3-deutero-N-cyclopropyl-2-hydroxyhexanamide hydrochloric acid salt

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

(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

(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

Conditions
ConditionsYield
With water; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0 - 25℃;
C13H24BNO3*ClH
1239375-12-2

C13H24BNO3*ClH

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

C40H61BN6O7

C40H61BN6O7

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine; HATU In dichloromethane; N,N-dimethyl-formamide at 20℃;
(3S)-3-amino-N-cyclopropyl-3-deutero-2-hydroxyhexanamide hydrochloride
950842-21-4

(3S)-3-amino-N-cyclopropyl-3-deutero-2-hydroxyhexanamide hydrochloride

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

(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

(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

Conditions
ConditionsYield
Stage #1: (1S,3aR,6aS)-2-((S)-2-((S)-2-cyclohexyl-2-(pyrazine-2-carboxamido)acetamido)-3,3-dimethylbutanoyl)octahydrocyclopenta[c]pyrrole-1-carboxylic acid With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; diisopropylamine In N,N-dimethyl-formamide at 20℃; for 0.25h;
Stage #2: (3S)-3-amino-N-cyclopropyl-3-deutero-2-hydroxyhexanamide hydrochloride In N,N-dimethyl-formamide for 24h;
3-(S)-3-amino-N-cyclopropyl-2-hydroxyhexanamide
402960-19-4

3-(S)-3-amino-N-cyclopropyl-2-hydroxyhexanamide

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

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

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

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

(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
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 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

(1S,3aR,6aS)-(2S)-2-Cyclohexyl-N-(2-pyrazinylcarbonyl)glycyl-3-methyl-L-valyloctahydrocyclopenta[c]pyrrole-1-carboxylic acid Specification

The (1S,3aR,6aS)-(2S)-2-Cyclohexyl-N-(2-pyrazinylcarbonyl)glycyl-3-methyl-L-valyloctahydrocyclopenta[c]pyrrole-1-carboxylic acid, with the CAS registry number 402958-98-9, is also known as Cyclopenta[c]pyrrole-1-carboxylic acid, (2S)-2-cyclohexyl-N-(pyrazinylcarbonyl)glycyl-3-methyl-L-valyloctahydro-, (1S,3aR,6aS)-. It belongs to the product categories of Aromatics; Chiral Reagents; Heterocycles; Intermediates & Fine Chemicals; Pharmaceuticals. This chemical's molecular formula is C27H39N5O5 and molecular weight is 513.63. What's more, its systematic name is (1S,3aR,6aS)-2-[(2S)-2-({(2S)-2-Cyclohexyl-2-[(2-pyrazinylcarbonyl)amino]acetyl}amino)-3,3-dimethylbutanoyl]octahydrocyclopenta[c]pyrrole-1-carboxylic acid.

Physical properties of (1S,3aR,6aS)-(2S)-2-Cyclohexyl-N-(2-pyrazinylcarbonyl)glycyl-3-methyl-L-valyloctahydrocyclopenta[c]pyrrole-1-carboxylic acid are: (1)ACD/LogP: 3.58±0.74; (2)# of Rule of 5 Violations: 2; (3)ACD/LogD (pH 5.5): 1.42; (4)ACD/LogD (pH 7.4): 0.00; (5)ACD/BCF (pH 5.5): 2.16; (6)ACD/BCF (pH 7.4): 1.00; (7)ACD/KOC (pH 5.5): 14.76; (8)ACD/KOC (pH 7.4): 1.00; (9)#H bond acceptors: 10; (10)#H bond donors: 3; (11)#Freely Rotating Bonds: 8; (12)Polar Surface Area: 141.59 Å2; (13)Index of Refraction: 1.567; (14)Molar Refractivity: 135.5±0.3 cm3; (15)Molar Volume: 414.6±3.0 cm3; (16)Polarizability: 53.7±0.5×10-24cm3; (17)Surface Tension: 55.7±3.0 dyne/cm; (18)Density: 1.2±0.1 g/cm3; (19)Flash Point: 448.3±34.3 °C; (20)Enthalpy of Vaporization: 124.6±3.0 kJ/mol; (21)Boiling Point: 817.7±65.0 °C at 760 mmHg; (22)Vapour Pressure: 0.0±3.1 mmHg at 25°C.

You can still convert the following datas into molecular structure:
(1)SMILES: CC(C)(C)[C@@H](C(=O)N1C[C@@H]2CCC[C@@H]2[C@H]1C(=O)O)NC(=O)[C@H](C3CCCCC3)NC(=O)c4cnccn4
(2)Std. InChI: InChI=1S/C27H39N5O5/c1-27(2,3)22(25(35)32-15-17-10-7-11-18(17)21(32)26(36)37)31-24(34)20(16-8-5-4-6-9-16)30-23(33)19-14-28-12-13-29-19/h12-14,16-18,20-22H,4-11,15H2,1-3H3,(H,30,33)(H,31,34)(H,36,37)/t17-,18-,20-,21-,22+/m0/s1
(3)Std. InChIKey: GUDVCEUDUGFATD-OOOLTRJPSA-N

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