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[ CAS No. 124832-27-5 ] {[proInfo.proName]}

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Chemical Structure| 124832-27-5
Chemical Structure| 124832-27-5
Structure of 124832-27-5 * Storage: {[proInfo.prStorage]}
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Product Details of [ 124832-27-5 ]

CAS No. :124832-27-5 MDL No. :MFCD11114398
Formula : C13H21ClN6O4 Boiling Point : -
Linear Structure Formula :- InChI Key :ZCDDBUOENGJMLV-QRPNPIFTSA-N
M.W : 360.80 Pubchem ID :135398741
Synonyms :
Valaciclovir hydrochloride;L-Valacyclovir (hydrochloride);BW 256U87;BW 256U;Valaciclovir HCl

Calculated chemistry of [ 124832-27-5 ]

Physicochemical Properties

Num. heavy atoms : 24
Num. arom. heavy atoms : 9
Fraction Csp3 : 0.54
Num. rotatable bonds : 8
Num. H-bond acceptors : 7.0
Num. H-bond donors : 3.0
Molar Refractivity : 89.51
TPSA : 151.14 Ų

Pharmacokinetics

GI absorption : Low
BBB permeant : No
P-gp substrate : Yes
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -8.37 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.0
Log Po/w (XLOGP3) : 0.19
Log Po/w (WLOGP) : -0.14
Log Po/w (MLOGP) : -0.52
Log Po/w (SILICOS-IT) : -0.24
Consensus Log Po/w : -0.14

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 1.0
Egan : 1.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -1.95
Solubility : 4.08 mg/ml ; 0.0113 mol/l
Class : Very soluble
Log S (Ali) : -2.92
Solubility : 0.431 mg/ml ; 0.0012 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.02
Solubility : 3.42 mg/ml ; 0.00948 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 2.0
Synthetic accessibility : 3.61

Safety of [ 124832-27-5 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 124832-27-5 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Upstream synthesis route of [ 124832-27-5 ]
  • Downstream synthetic route of [ 124832-27-5 ]

[ 124832-27-5 ] Synthesis Path-Upstream   1~6

  • 1
  • [ 124832-31-1 ]
  • [ 124832-27-5 ]
YieldReaction ConditionsOperation in experiment
92% With hydrogenchloride; 5%-palladium/activated carbon; hydrogen In water at 25 - 30℃; To a 1L capacity hydrogenator charged a compound of formula II (50g), concentrated hydrochloric acid (9.6ml), 5percent palladium on carbon (5g) and water (350ml) and hydrogenate the reaction mass under hydrogen pressure of 3 kg/cm 2 to 8 kg/cm 2 at a temperature of 25-30°C for 6 to 12 hours. The reaction mass was filtered under vacuum and washed with water. The filtrate was then distilled off under vacuum. The reaction mass was then cooled and isopropyl alcohol was added to the reaction mass. The reaction mass was further cooled to a temperature of 5-10°C and maintained for 1 hour. The product valacyclovir hydrochloride obtained was filtered and washed with isopropyl alcohol.Yield 92percent and purity 99.8percentANALYTICAL METHOD FOR ANALYSISHPLC column : USP LI, 4.6 x 150 mm, 3.5 ???(Zorbax SB-C18, Part No. 863953-914)Detector : UV 250nmMobile phase A : In a 1000ml volumetric flask add 2.8ml of triethylamine, 800ml of purified water and adjust the pH to 5.00 + 0.05 with glacial acetic acid. Complete the volume with purified water.Mobile Phase B AcetonitrileInjection volume 50??,Column temperature 30°CFlow rate l.OmL/minutesGradient
92% With hydrogenchloride; 5%-palladium/activated carbon; hydrogen In water at 25 - 30℃; To a 1L capacity hydrogenator charged a compound of formula II (50 g), concentrated hydrochloric acid (9.6 ml), 5percent palladium on carbon (5 g) and water (350 ml) and hydrogenate the reaction mass under hydrogen pressure of 3 kg/cm2 to 8 kg/cm2 at a temperature of 25-30° C. for 6 to 12 hours. The reaction mass was filtered under vacuum and washed with water. The filtrate was then distilled off under vacuum. The reaction mass was then cooled and isopropyl alcohol was added to the reaction mass. The reaction mass was further cooled to a temperature of 5-10° C. and maintained for 1 hour. The product valacyclovir hydrochloride obtained was filtered and washed with isopropyl alcohol. Yield 92percent and purity 99.8percent
Reference: [1] Asian Journal of Chemistry, 2010, vol. 22, # 5, p. 4092 - 4098
[2] Patent: WO2013/76688, 2013, A1, . Location in patent: Page/Page column 10-11
[3] Patent: US2014/296520, 2014, A1, . Location in patent: Paragraph 0043
[4] Journal of Pharmaceutical Sciences, 2001, vol. 90, # 10, p. 1505 - 1515
[5] Patent: WO2006/35452, 2006, A1, . Location in patent: Page/Page column 5-6
[6] Patent: US2007/112193, 2007, A1, . Location in patent: Page/Page column 6; 7
[7] Patent: US2007/112193, 2007, A1, . Location in patent: Page/Page column 6-7
[8] Patent: US2007/112193, 2007, A1, . Location in patent: Page/Page column 7
  • 2
  • [ 124832-31-1 ]
  • [ 124832-27-5 ]
Reference: [1] Patent: US6107302, 2000, A,
  • 3
  • [ 502421-44-5 ]
  • [ 124832-27-5 ]
YieldReaction ConditionsOperation in experiment
31 g With hydrogenchloride In methanol; dichloromethane; water at 80℃; Flow reactor Preparation of Solution-A Boc-L-Valacyclovir crude (50 g) was charged into mixture of methylene chloride (375 ml) and methanol (125 ml) at 25-30°C and stirred the reaction mass at 25- 30°C to get the clear solution-A. Preparation of Solution-B Cone. Hydrochloric acid (56 ml) was added to DM water (224 ml) over a period of 15-20 min at 20-25°C. Thereafter methanol (56 ml) was added slowly to the obtained solution at 20-25°C. Above separately prepared solution-A (Flow rate-8 ml/min) and solution-B (Flow rate-5.5 ml/min) were fed to the continuous flow micro reactor at 80°C. The elute reaction mass from micro reactor was continuously collected at 0-5°C. As the feed solutions A & B are consumed micro reactor is flush with methylene chloride (50 ml: 50 ml) each feed. Immediately after the collection of reaction mass, aqueous layer and lower organic layers were separated. The pH of the aqueous layer containing product was adjusted to about 2.5 to 2.8 with triethyl amine (~ 46.28 g) at 0-5 °C). Ethanol (300 ml) at 0-5°C was added slowly to the solution. The obtained reaction mass was distilled under reduced pressure (400-40 mm Hg) to get white. The obtained solid mass was cooled at 25-30°C and ethanol (300 ml) was added and continued stirring the above slurry mass at 25-30°C for 60-80 min. The solid was filtered and washed with chill ethanol (100 ml. 0-5°C). The obtained solid is dried in vacuum dryer at 40-45°C till moisture content is 5-8percent. Yield: 31 g Purity: 99percent (by HPLC)
Reference: [1] Patent: WO2017/149420, 2017, A1, . Location in patent: Page/Page column 13-15
  • 4
  • [ 124832-26-4 ]
  • [ 124832-27-5 ]
Reference: [1] Patent: US2007/112193, 2007, A1, . Location in patent: Page/Page column 8
[2] Patent: US2007/112193, 2007, A1, . Location in patent: Page/Page column 8
[3] Patent: US2007/112193, 2007, A1, . Location in patent: Page/Page column 8
[4] Patent: US2007/112193, 2007, A1, . Location in patent: Page/Page column 8
[5] Patent: US2007/112193, 2007, A1, . Location in patent: Page/Page column 8
  • 5
  • [ 59277-89-3 ]
  • [ 124832-27-5 ]
Reference: [1] Journal of Pharmaceutical Sciences, 2001, vol. 90, # 10, p. 1505 - 1515
  • 6
  • [ 102728-64-3 ]
  • [ 124832-27-5 ]
Reference: [1] Journal of Pharmaceutical Sciences, 2001, vol. 90, # 10, p. 1505 - 1515
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