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[ CAS No. 635728-49-3 ] {[proInfo.proName]}

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Chemical Structure| 635728-49-3
Chemical Structure| 635728-49-3
Structure of 635728-49-3 * Storage: {[proInfo.prStorage]}
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Product Details of [ 635728-49-3 ]

CAS No. :635728-49-3 MDL No. :
Formula : C29H43N3O8S Boiling Point : -
Linear Structure Formula :- InChI Key :QWSHKNICRJHQCY-VBTXLZOXSA-N
M.W : 593.73 Pubchem ID :23725083
Synonyms :
TMC114 Ethanolate;Darunavir (ethanolate);UIC 94017;TMC-114

Calculated chemistry of [ 635728-49-3 ]

Physicochemical Properties

Num. heavy atoms : 41
Num. arom. heavy atoms : 12
Fraction Csp3 : 0.55
Num. rotatable bonds : 13
Num. H-bond acceptors : 9.0
Num. H-bond donors : 4.0
Molar Refractivity : 155.09
TPSA : 169.03 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 : Yes
Log Kp (skin permeation) : -7.9 cm/s

Lipophilicity

Log Po/w (iLOGP) : 4.67
Log Po/w (XLOGP3) : 2.85
Log Po/w (WLOGP) : 3.46
Log Po/w (MLOGP) : 0.81
Log Po/w (SILICOS-IT) : 1.46
Consensus Log Po/w : 2.65

Druglikeness

Lipinski : 2.0
Ghose : None
Veber : 2.0
Egan : 1.0
Muegge : 1.0
Bioavailability Score : 0.17

Water Solubility

Log S (ESOL) : -4.68
Solubility : 0.0125 mg/ml ; 0.0000211 mol/l
Class : Moderately soluble
Log S (Ali) : -6.06
Solubility : 0.000519 mg/ml ; 0.000000874 mol/l
Class : Poorly soluble
Log S (SILICOS-IT) : -5.33
Solubility : 0.00276 mg/ml ; 0.00000466 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 2.0
Synthetic accessibility : 6.04

Safety of [ 635728-49-3 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 635728-49-3 ]

* 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 [ 635728-49-3 ]
  • Downstream synthetic route of [ 635728-49-3 ]

[ 635728-49-3 ] Synthesis Path-Upstream   1~6

  • 1
  • [ 64-17-5 ]
  • [ 192725-55-6 ]
  • [ 169280-56-2 ]
  • [ 635728-49-3 ]
YieldReaction ConditionsOperation in experiment
82.5%
Stage #1: at -4 - 30℃; for 10 h;
Stage #2: at 45 - 50℃; for 1 h;
A solution of (3R,3aS,6aR)-hexahydrofuro[2,3-t]furan-3-yl 4-nitrophenyl carbonate (5b, 75.4 g) in N-methyl-2-pyrrolidinone (300 mL) was added to a pre-cooled (-2±2° C.) solution of the compound of formula 4 (100 g) in N-methyl-2-pyrrolidinone (200 mL) at -4 to 0° C. over a period of 2 h.
The temperature of the reaction mass was slowly raised to 25-30° C. and maintained for 8 h.
After completion of the reaction (TLC monitoring), ethyl acetate (1000 mL) and purified water (500 mL) were added to the reaction mass.
The layers were separated; organic layer was washed with sodium carbonate solution (2*500 mL) followed by sodium chloride solution.
The organic layer was concentrated; ethanol (300 mL) was added, heated to 45-50° C., maintained for 1 h, filtered and washed with ethanol.
The wet compound was taken into a mixture of ethyl acetate-ethanol (7:93, 600 mL), heated to reflux, charcoal was added and filtered.
The resultant filtrate was cooled to 0-5° C., filtered the separated solid and washed with ethanol.
The wet compound was dried at 45° C. to obtain the in 124.3 g (yield-82.5percent).
The obtained Darunavir ethanolate had purity of 99.79percent on area by HPLC and contained 0.08percent on area by HPLC of the difuranyl impurity.
Reference: [1] Patent: US2012/251826, 2012, A1, . Location in patent: Page/Page column 10
  • 2
  • [ 64-17-5 ]
  • [ 635728-49-3 ]
Reference: [1] Patent: WO2011/51978, 2011, A2, . Location in patent: Page/Page column 13
  • 3
  • [ 98760-08-8 ]
  • [ 635728-49-3 ]
Reference: [1] Patent: US2012/251826, 2012, A1,
  • 4
  • [ 191226-98-9 ]
  • [ 635728-49-3 ]
Reference: [1] Patent: US2012/251826, 2012, A1,
  • 5
  • [ 160232-08-6 ]
  • [ 635728-49-3 ]
Reference: [1] Patent: US2012/251826, 2012, A1,
  • 6
  • [ 183004-94-6 ]
  • [ 635728-49-3 ]
Reference: [1] Patent: US2012/251826, 2012, A1,
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