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

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

 EINECS N/A
CAS No. 402958-98-9 Density 1.2±0.1 g/cm3
PSA 148.57000 LogP 3.75090
Solubility N/A Melting Point N/A
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 N/A Appearance N/A
Safety Risk Codes N/A
Molecular Structure Molecular Structure of 402958-98-9 (Des[N-[(1S)-1-[2-(cyclopropylaMino)-2-oxoacetyl]butyl]carboxaMido] 1-Carboxy Telaprevir) Hazard Symbols N/A
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

Article Data 3

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

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

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
98-97-5

2-pyrazylcarboxylic acid

piperazine-derivatized ArgoGelTM Wang resin

piperazine-derivatized ArgoGelTM Wang resin

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
63038-27-7

L-tert-leucine methyl ester hydrochloride

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
109183-71-3

N-(tert-butoxycarbonyl)-L-cyclohexylglycine

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
402958-93-4

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

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
402958-96-7

(S)-2-((S)-2-cyclohexyl-2-(pyrazine-2-carboxamido)acetamido)-3,3-dimethylbutanoic 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
402958-95-6

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

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

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
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

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;
402958-25-2

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

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

(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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