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[ CAS No. 229613-93-8 ] {[proInfo.proName]}

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Chemical Structure| 229613-93-8
Chemical Structure| 229613-93-8
Structure of 229613-93-8 * Storage: {[proInfo.prStorage]}
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Product Details of [ 229613-93-8 ]

CAS No. :229613-93-8 MDL No. :MFCD18206350
Formula : C18H30N2O5 Boiling Point : -
Linear Structure Formula :- InChI Key :WYUYCGDXMIJIAZ-KYEXWDHISA-N
M.W : 354.44 Pubchem ID :10522092
Synonyms :

Calculated chemistry of [ 229613-93-8 ]

Physicochemical Properties

Num. heavy atoms : 25
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.83
Num. rotatable bonds : 9
Num. H-bond acceptors : 6.0
Num. H-bond donors : 1.0
Molar Refractivity : 98.31
TPSA : 86.22 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : Yes
Log Kp (skin permeation) : -6.52 cm/s

Lipophilicity

Log Po/w (iLOGP) : 3.32
Log Po/w (XLOGP3) : 2.74
Log Po/w (WLOGP) : 2.5
Log Po/w (MLOGP) : 1.94
Log Po/w (SILICOS-IT) : 2.56
Consensus Log Po/w : 2.61

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.17
Solubility : 0.24 mg/ml ; 0.000676 mol/l
Class : Soluble
Log S (Ali) : -4.21
Solubility : 0.0221 mg/ml ; 0.0000624 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -3.01
Solubility : 0.346 mg/ml ; 0.000977 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 2.0
Synthetic accessibility : 5.01

Safety of [ 229613-93-8 ]

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 [ 229613-93-8 ]

* 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 [ 229613-93-8 ]
  • Downstream synthetic route of [ 229613-93-8 ]

[ 229613-93-8 ] Synthesis Path-Upstream   1~10

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YieldReaction ConditionsOperation in experiment
97.13%
Stage #1: With potassium carbonate; sodium hydroxide In water; acetoneIndustry scale
Stage #2: at 30 - 45℃;
Stage #3: With ammonia In methanol; water; acetone at 0 - 20℃; for 1.25 h; Industry scale
1,1-dimethylethyl ammonium (3aR,4R,6S,6aS)-4-[[(1,1-dimethylethoxy) carbonyl] amino]-3-(1'-ethylpropyl)-3a,5,6,6a-tetrahydro-4H-cyclopenta[d]isooxazole-6-carboxylate (16) (3210 g, 7.8 mol) was suspended in acetone (4000 g).
Potassium carbonate (53.8 g), and an aqueous solution of 30percent sodium hydroxide containing 312 g of sodium hydroxide were added to the resulting suspension.
3000 ml of solvent was removed by evaporation, 3000 ml of acetone was added, then, 3000 ml of solvent was removed by evaporation, 3000 ml of acetone was added, and thereafter 4000 ml acetone was removed by evaporation, obtaining a reaction solution substantially free of the odor of tert-butylamine.
The reaction solution was cooled down to 30 - 35°C, to which 1060 ml of dimethyl sulfate was added dropwise at a speed to keep the temperature not exceeding 45°C.
After completion of the addition, the resulting reaction mixture was stirred at 40 - 45°C for 1.5 hours.
The reaction mixture was cooled down to 15 - 20°C, to which was then added 1500 ml of 25percent ammonia.
After stirring for 30 minutes, 1500 ml of methanol was added, and then the reaction mixture was cooled down to 0 - 5°C.
Thereafter, 2240 ml of 25percent ammonia was added to the reaction mixture within 45 minutes.
The resulting product was collected by filtration, washed with 3000 ml of water, and dried under vacuum at 45 - 50°C. Finally, 2686.2 g of a product was obtained, with a yield of 97.13percent.
Reference: [1] Patent: EP2186795, 2010, A1, . Location in patent: Page/Page column 6; 11-12
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YieldReaction ConditionsOperation in experiment
57% With sodium hypochlorite; triethylamine In dichloromethane for 44 h; Reflux (+)-Methyl (3aR,4R,6S,6aS)-4-[(tert-butoxycarbonyl)-amino]-3-(1-ethylpropyl)-4,5,6,6a-tetrahydro-3aH-cyclopenta[d]isoxazole-6-carboxylate (86)
To a mixture of olefin 85 (1.3 g, 5.4 mmol), 2-ethylbutanal oxime (4.2 g, 36.5 mmol), and Et3N (0.34 mL, 2.4 mmol) in CH2Cl2 (12 mL) was added bleach (34.7 mL of 13percent NaOCl aqueous solution, 72.7 mmol).
The mixture was heated at reflux for 44 h, and monitored for completion by TLC.
The mixture was extracted with CH2Cl2 (3*45 mL).
The combined organic layers were washed with water and brine, dried over anhydrous Mg2SO4, filtered, and concentrated by rotary evaporation.
The residue was purified by silica gel flash column chromatography (EtOAc/hexane gradients, 1:12 to 1:9 to 1:6) to give compound 86 (1.1 g, 57percent). C18H30N2O5; pale yellow oil; 1H NMR (400 MHz, CDCl3) δ 5.57 (1H, d, J=7.2 Hz), 5.17 (1H, d, J=9.2 Hz), 4.19 (1H, br s), 3.73 (3H, s), 3.56 (1H, d, J=9.6 Hz), 3.16 (1H, d, J=7.6 Hz), 2.50-2.46 (1H, m), 2.12-2.05 (1H, m), 2.02-1.97 (1H, m), 1.74-1.55 (4H, m), 1.41 (9H, s), 0.92-0.84 (6H, m); 13C NMR (100 MHz, CDCl3) δ 174.4, 160.5, 154.3, 87.0, 79.5, 63.6, 55.7, 52.7, 52.3, 40.7, 33.6, 28.7, 26.0, 24.3, 12.5, 11.2; ESI-HRMS calcd. for C18H31N2O5: 355.2233, found: m/z 355.2233 [M+H]+.
Reference: [1] Journal of Medicinal Chemistry, 2016, vol. 59, # 11, p. 5297 - 5310
[2] Patent: US2013/274229, 2013, A1, . Location in patent: Paragraph 0332
  • 3
  • [ 5399-18-8 ]
  • [ 168683-02-1 ]
  • [ 229613-93-8 ]
Reference: [1] Synthetic Communications, 2013, vol. 43, # 19, p. 2641 - 2647
  • 4
  • [ 7796-76-1 ]
  • [ 168683-02-1 ]
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Reference: [1] Journal of Medicinal Chemistry, 2000, vol. 43, # 19, p. 3482 - 3486
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  • [ 7796-76-1 ]
  • [ 103-71-9 ]
  • [ 168683-02-1 ]
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Reference: [1] Journal of Medicinal Chemistry, 2001, vol. 44, # 25, p. 4379 - 4392
  • 6
  • [ 79200-56-9 ]
  • [ 229613-93-8 ]
Reference: [1] Journal of Medicinal Chemistry, 2000, vol. 43, # 19, p. 3482 - 3486
[2] Synthetic Communications, 2013, vol. 43, # 19, p. 2641 - 2647
[3] Journal of Medicinal Chemistry, 2016, vol. 59, # 11, p. 5297 - 5310
  • 7
  • [ 229613-83-6 ]
  • [ 229613-93-8 ]
Reference: [1] Synthetic Communications, 2013, vol. 43, # 19, p. 2641 - 2647
[2] Patent: US2013/274229, 2013, A1,
[3] Journal of Medicinal Chemistry, 2016, vol. 59, # 11, p. 5297 - 5310
  • 8
  • [ 168683-02-1 ]
  • [ 229613-93-8 ]
Reference: [1] Patent: CN106928097, 2017, A, . Location in patent: Paragraph 0106; 0109
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  • [ 138923-03-2 ]
  • [ 229613-93-8 ]
Reference: [1] Journal of Medicinal Chemistry, 2000, vol. 43, # 19, p. 3482 - 3486
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Reference: [1] Patent: CN106928097, 2017, A,
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