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[ CAS No. 165450-17-9 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 165450-17-9
Chemical Structure| 165450-17-9
Chemical Structure| 165450-17-9
Structure of 165450-17-9 * Storage: {[proInfo.prStorage]}
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Product Details of [ 165450-17-9 ]

CAS No. :165450-17-9 MDL No. :MFCD09039056
Formula : C20H30N2O5 Boiling Point : -
Linear Structure Formula :- InChI Key :HLIAVLHNDJUHFG-HOTGVXAUSA-N
M.W : 378.46 Pubchem ID :9810996
Synonyms :
Chemical Name :(S)-3-((3,3-Dimethylbutyl)amino)-4-(((S)-1-methoxy-1-oxo-3-phenylpropan-2-yl)amino)-4-oxobutanoic acid

Calculated chemistry of [ 165450-17-9 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 27
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.55
Num. rotatable bonds : 13
Num. H-bond acceptors : 6.0
Num. H-bond donors : 3.0
Molar Refractivity : 102.5
TPSA : 104.73 Ų

Pharmacokinetics

GI absorption : High
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) : -8.71 cm/s

Lipophilicity

Log Po/w (iLOGP) : 3.3
Log Po/w (XLOGP3) : -0.14
Log Po/w (WLOGP) : 1.76
Log Po/w (MLOGP) : 1.72
Log Po/w (SILICOS-IT) : 2.75
Consensus Log Po/w : 1.88

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.4
Solubility : 14.9 mg/ml ; 0.0394 mol/l
Class : Very soluble
Log S (Ali) : -1.61
Solubility : 9.39 mg/ml ; 0.0248 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -4.77
Solubility : 0.00649 mg/ml ; 0.0000171 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 2.0
Synthetic accessibility : 3.59

Safety of [ 165450-17-9 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H332-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 165450-17-9 ]

* 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 [ 165450-17-9 ]
  • Downstream synthetic route of [ 165450-17-9 ]

[ 165450-17-9 ] Synthesis Path-Upstream   1~2

  • 1
  • [ 2987-16-8 ]
  • [ 22839-47-0 ]
  • [ 165450-17-9 ]
YieldReaction ConditionsOperation in experiment
85% With hydrogen In methanol; water at 20℃; for 6 h; In a reactor being equipped with an agitating blade and permitting markedly smooth transfer of gaseous hydrogen into the liquid layer, the following substances were charged with stirring: 550 mL of ion-exchanged water, 1100 mL of methanol, 61 g of aspartame, 20 g of 10percent palladium-carbon (having a water content of 50 wt. percent) and 19 g of 3,3-dimethylbutyl aldehyde.After the completion of charging, hydrogen gas was introduced at a flow rate of 200 mL/min while the mixture was continued to be stirred at room temperature. The progress of the reaction was monitored by sampling the reaction mixture and analyzing the resulting products in the samplers by high-performance liquid chromatography (HPLC). After six hours' reaction, the reactor was filled with a nitrogen gas stream, followed by filtration through a microporous filter (0.50 μm) to remove the catalyst. The filtrate (1,460 g), when analyzed, revealed that the N-(3,3-dimethylbutyl)-APM had been produced in an amount of 64 g (yield: 85percent).The filtrate was then concentrated to 497 g, whereby crystals were precipitated. The resulting slurry was heated at 70° C. to dissolve the crystals. Then, the resulting solution was analyzed by gas chromatography, and revealed that the methanol content in the solution was 8.15 wt. percent.Subsequently, this uniform solution of N-(3,3-dimethylbutyl)-APM was gradually cooled from 70° C. to 40° C. and maintained at 40° C. for 1 hour, whereby nucleation was generated spontaneously.Next, the resulting slurry was then cooled to 5° C. at a cooling rate of 5° C./hour, and aged overnight at this temperature, followed by separating the crystals by filtration.As a result of measuring the diffracted X-rays by using CuKα rays in accordance with the powder X-ray diffraction method, the wet crystals thus separated showed the specific peaks of diffracted X-rays at angles of diffraction (2ψ, CuKα rays) of at least 6.0°, 24.8°, 8.2° and 16.5°, indicating that the resulting crystals were A-type crystals. The powder X-ray diffraction pattern at this time will be shown in FIG. 3. And, the water content of the crystals was found to be 51.14 wt. percent as measured directly by the Karl Fisher's method.The above-described wet crystal's were then dried at 50° C. under reduced pressure until the water content became 5.8 wt. percent, whereby 58 g of N-(3,3-dimethylbutyl)-APM was obtained (yield: 72percent, and a purity of 97percent by HPLC). As a result of measuring the diffracted X-rays in accordance with the powder X-ray diffraction method, the dried crystals showed the specific peaks of diffracted X-rays at angles of diffraction (2ψ, CuKaα rays) of at least 6.0°, 24.8°, 8.2° and 16.5°, indicating that the resulting dry crystals were also A-type crystals. The powder X-ray diffraction pattern at this time will be shown in FIG. 4. The IR spectrum data of these crystals were completely identical to those described in WO95/30689.
Reference: [1] Patent: US6914151, 2005, B1, . Location in patent: Page/Page column 5-6
[2] Acta Crystallographica Section C: Crystal Structure Communications, 1999, vol. 55, # 8, p. 1365 - 1368
[3] Synthetic Communications, 1999, vol. 29, # 24, p. 4461 - 4467
  • 2
  • [ 22839-65-2 ]
  • [ 165450-17-9 ]
Reference: [1] Patent: CN105585514, 2016, A, . Location in patent: Paragraph 0036; 0037
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