(S)-2-((S)-2-CYCLOHEXYL-2-[(PYRAZINE-2-CARBONYL)-AMINO]-ACETYLAMINO)-3,3-DIMETHYL-BUTYRIC ACID CAS#: 402958-96-7; 凯望编码 (ChemWhat Code): 91941

IdentificationPhysical DataSpectra
Route of Synthesis (ROS)Safety and HazardsOther Data

Identification

英文名(S)-2-((S)-2-CYCLOHEXYL-2-[(PYRAZINE-2-CARBONYL)-AMINO]-ACETYLAMINO)-3,3-DIMETHYL-BUTYRIC ACID
IUPAC Name(2S)-2-[[(2S)-2-cyclohexyl-2-(pyrazine-2-carbonylamino)acetyl]amino]-3,3-dimethylbutanoic acid 
分子结构S-2-S-2-CYCLOHEXYL-2-PYRAZINE-2-CARBONYL-AMINO-ACETYLAMINO-33-DIMETHYL-BUTYRIC-ACID-CAS-402958-96-7
CAS编号 402958-96-7
MDL NumberMFCD11865138
别名402958-96-7
(S)-2-((S)-2-Cyclohexyl-2-(pyrazine-2-carboxamido)acetamido)-3,3-dimethylbutanoic acid
(2S)-2-Cyclohexyl-N-(2-pyrazinylcarbonyl)glycyl-3-methyl-L-valine
(2S)-2-[[(2S)-2-cyclohexyl-2-(pyrazine-2-carbonylamino)acetyl]amino]-3,3-dimethylbutanoic acid
(S)-2-((S)-2-CYCLOHEXYL-2-[(PYRAZINE-2-CARBONYL)-AMINO]-ACETYLAMINO)-3,3-DIMETHYL-BUTYRIC ACID
(S)-2-((S)-2-Cyclohexyl-2-(pyrazine-2-carboxamido)-acetamido)-3,3-dimethylbutanoic acid
(S)-2-{(S)-2-cyclohexyl-2-[(pyrazine-2-carbonyl)-amino]-acetylamino-3,3-dimethyl-butyric acid
(S)-2-{(S)-2-Cyclohexyl-2-[(pyrazine-2-carbonyl)-amino]-acetylamino}-3,3-dimethyl-butyric acid
BZUKJNKTPCZNPM-LSDHHAIUSA-N
L-Valine, (2S)-2-cyclohexyl-N-(pyrazinylcarbonyl)glycyl-3-methyl-
L-Valine, (2S)-2-cyclohexyl-N-(2-pyrazinylcarbonyl)glycyl-3-methyl-
SCHEMBL1013600
DTXSID60678628
CS-M1866
HY-I0115
MFCD11865138
AKOS016007986
(S)-2-((S)-2-Cyclohexyl-2-(pyrazine-2-carboxamido)-acetamido)-3,3-dimethylb utanoic acid
AC-26317
CS-13256
DA-69063
PD163439
A852379
J-502386
(s)-2-((s)-2-cyclohexyl-2-(pyrazine-2-carboxamido)acetamido)-3,3-dimethyl butanoic acid
(S)-2-((S)-2-Cyclohexyl-2-(pyrazine-2-carboxamido)acetamido)-3,3-dimethylbutanoicacid
N-{(2S)-2-Cyclohexyl-2-[(2-pyrazinylcarbonyl)amino]acetyl}-3-methyl-L-valine
N-{(2S)-2-Cyclohexyl-2-[(pyrazine-2-carbonyl)amino]acetyl}-3-methyl-L-valine
(2S)-2-[[(2S)-2-cyclohexyl-2-(pyrazine-2-carbonylamino)acetyl]amino]-3,3-dimethyl-butanoic acid
(S)-2-(N-(2-aminoacetyl)pyrazine-2-carboxamido)-2-cyclohexyl-3,3-dimethylbutanoic acid;(S)-2-((S)-2-Cyclohexyl-2-(pyrazine-2-carboxamido)acetamido)-3,3-dimethylbutanoic acid
分子式C19H28N4O4
分子量376.4
InChIInChI=1S/C19H28N4O4/c1-19(2,3)15(18(26)27)23-17(25)14(12-7-5-4-6-8-12)22-16(24)13-11-20-9-10-21-13/h9-12,14-15H,4-8H2,1-3H3,(H,22,24)(H,23,25)(H,26,27)/t14-,15+/m0/s1
InChI KeyBZUKJNKTPCZNPM-LSDHHAIUSA-N
Isomeric SMILESCC(C)(C)[C@@H](C(=O)O)NC(=O)[C@H](C1CCCCC1)NC(=O)C2=NC=CN=C2 

Physical Data

AppearancePowder

Spectra

Description (NMR Spectroscopy)Nucleus (NMR Spectroscopy)Solvents (NMR Spectroscopy)Frequency (NMR Spectroscopy), MHz
Spectrum1H
Chemical shifts1HCD3OD300
Chemical shifts13CCD3OD100
1Hchloroform-d1250.13
Chemical shifts1Hchloroform-d1250.1
Chemical shifts13Cchloroform-d162.9
Description (IR Spectroscopy)
Neat (no solvent)
Bands

Route of Synthesis (ROS)

Route of Synthesis (ROS) of (S)-2-((S)-2-CYCLOHEXYL-2-[(PYRAZINE-2-CARBONYL)-AMINO]-ACETYLAMINO)-3,3-DIMETHYL-BUTYRIC ACID CAS 402958-96-7
Route of Synthesis (ROS) of (S)-2-((S)-2-CYCLOHEXYL-2-[(PYRAZINE-2-CARBONYL)-AMINO]-ACETYLAMINO)-3,3-DIMETHYL-BUTYRIC ACID CAS 402958-96-7
ConditionsYield
With sodium hydroxide In methanol100%
With water; sodium hydroxide In tetrahydrofuran; methanol at 20℃;95%
Stage #1: (S)-methyl 2-((S)-2-cyclohexyl-2-(pyrazine-2-carboxamido)acetamido)-3,3-dimethylbutanoate With sodium hydroxide In tetrahydrofuran; methanol at 0 – 20℃;
Stage #2: With potassium hydrogensulfate In water pH=3.5;

Experimental Procedure
A solution of 1 M NaOH (0.94 ml, 0.94 mmol) was added to a solution of 11 (0.31 g, 0.78 mmol) in THF (3 ml) at 0°C. MeOH was added to the formed suspension, to give a clear and colourless solution. The reaction mixture was stirred overnight at room temperature, followed by concentration in vacuo. The pH of this aqueous layer was set to 3.5 with 1 M KHSO4 and subsequently extracted with EtOAc (2 χ 10ml). The mixture was dried with Na2S04, filtered, and concentrated in vacuo, to give 2 (0.28 g, 0.75 mmol, 95%) as a white solid.[a f° = +21.7 (c= 1.015, CHC13); *H NMR (250.13 MHz, CDC13): δ = 9.39 (d, J= 1.3Hz, 1H), 8.77 (d, J = 2.5 Hz, 1H), 8.57 (dd, J = 1.5, 2.5 Hz, 1H), 8.35 (d, J = 9 Hz, 1H), 6.70 (d, J = 9.0 Hz, 1H), 4.45 (t, J = 8.8 Hz, 1H), 4.42 (d, J = 9.2 Hz, 1H), 1.94 (m, 1H), 1.71 (m, 5H), 1.20 (m, 5H), 1.01 (s, 9H); 13C NMR (62.90 MHz, CDCI3): δ = 173.4 (C), 170.5 (C), 163.3 (C), 147.4 (CH), 144.4 (CH), 144.2 (C), 142.8 (CH), 58.4 (CH), 51.9 (CH), 40.4 (CH), 34.7 (C), 29.8 (CH2), 28.6 (CH2), 26.6 (CH3), 25.8 (CH2); IR (neat): v„(cm ) = 3335 (w), 2930 (m), 1726 (m), 1663 (s), 1514 (s); HRMS (ESI, 4500 V): m/z calc. for Ci9H29N404Na+ ([M + Na]+) 399.2003, found 399.2013.		95%
With water; sodium hydroxide In methanol at 40 – 45℃; for 24h; Inert atmosphere;


Experimental Procedure
3 Synthesis of (S)-2-((S)-2-cyclohexyl-2-(pyrazine-2- carboxamido)acetamido)-3,3-dimethylbutanoic acid (II)
A 1M aqueous solution of sodium hydroxide (440 ml, 440 mmol) is added to a solution of methyl (S)-2-((S)-2-cyclohexyl-2-(pyrazine-2- carboxamido)-3,3-dimethylbutanoate (28.7 g, 73.5 mmol) in methanol(150 ml) maintained under inert atmosphere, and the mixture is heated to 40-45 °C and maintained under stirring for 24 hours. The mixture is acidified with 37% hydrochloric acid to a pH of 1 -2 and extracted with ethyl acetate (3×200 ml); the combined organic phases are washed with a saturated solution of sodium chloride (200 ml), dried with sodium sulphate, and concentrated to residue. The crude product obtained is taken up with ethyl acetate, heated at reflux temperature for about an hour and cooled in 4-5 hours to 0-5°C, and the solid is filtered by washing with ethyl acetate (3×50 ml). The solid is dried at 45-50°C at low pressure and 26.5 g of crystalline product is obtained, with an HPLC purity of 99.7% and a yield of 95%. -NMR 300 MHz, δ (CD3OD): 9,23 (s, 1H); 8,77 (s, 1H); 8,66 (s, 1H); 8,30 (bd, J=9Hz, 1H); 4,65 (d, J=7Hz, 1H); 4,32-4,30 (m, 1H); 1 ,88-1 ,59 (m, 6H); 1 ,24-1 ,07 (m, 5H); 0,99 (s, 9H). 13C-NM 100 MHz, δ (CD3OD): 172,05; 171 ,45; 162,95; 147,06; 143,95; 143,08; 142,93; 60,38; 57,77; 39,91 ; 33,09; 28,07; 26,26; 25,91 ; 25,56; 25,21 ; 24,84. MS(ES+): m/z 399 [M+Na]+.		95%
With lithium hydroxide In tetrahydrofuran; methanol; water at 20℃; for 6h;

Safety and Hazards

Pictogram(s)exclamation-mark
SignalWarning
GHS Hazard StatementsH302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]
Precautionary Statement CodesP264, P270, P301+P317, P330, and P501
(The corresponding statement to each P-code can be found at the GHS Classification page.)

Other Data

TransportationStore at 2~8° for long time.
HS Code
StorageStore at 2~8° for long time.
Shelf Life1 year
Market Price
Druglikeness
Lipinski rules component
分子量376.456
logP-0.476
HBA8
HBD3
Matching Lipinski Rules4
Veber rules component
Polar Surface Area (PSA)121.28
Rotatable Bond (RotB)9
Matching Veber Rules2
Use Pattern
2S-2-Cyclohexyl-N-2-pyrazinylcarbonylglycyl-3-methyl-L-valine (CAS 402958-96-7) is an important intermediate in the synthesis of Telaprevir. Telaprevir is a protease inhibitor used in the treatment of hepatitis C virus (HCV) infection.

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