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[ CAS No. 159749-28-7 ] {[proInfo.proName]}

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Chemical Structure| 159749-28-7
Chemical Structure| 159749-28-7
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Product Details of [ 159749-28-7 ]

CAS No. :159749-28-7 MDL No. :MFCD01861756
Formula : C9H15NO4 Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 201.22 Pubchem ID :-
Synonyms :

Calculated chemistry of [ 159749-28-7 ]

Physicochemical Properties

Num. heavy atoms : 14
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.78
Num. rotatable bonds : 4
Num. H-bond acceptors : 4.0
Num. H-bond donors : 1.0
Molar Refractivity : 53.56
TPSA : 66.84 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 : No
Log Kp (skin permeation) : -6.91 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.07
Log Po/w (XLOGP3) : 0.87
Log Po/w (WLOGP) : 0.7
Log Po/w (MLOGP) : 0.43
Log Po/w (SILICOS-IT) : -0.06
Consensus Log Po/w : 0.8

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 0.0
Bioavailability Score : 0.56

Water Solubility

Log S (ESOL) : -1.37
Solubility : 8.55 mg/ml ; 0.0425 mol/l
Class : Very soluble
Log S (Ali) : -1.86
Solubility : 2.79 mg/ml ; 0.0139 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -0.1
Solubility : 162.0 mg/ml ; 0.804 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.59

Safety of [ 159749-28-7 ]

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 [ 159749-28-7 ]

* 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 [ 159749-28-7 ]
  • Downstream synthetic route of [ 159749-28-7 ]

[ 159749-28-7 ] Synthesis Path-Upstream   1~8

  • 1
  • [ 24424-99-5 ]
  • [ 2133-34-8 ]
  • [ 159749-28-7 ]
YieldReaction ConditionsOperation in experiment
63.1%
Stage #1: With 4-methyl-morpholine In 1,4-dioxane; water at 0 - 25℃; for 22 h;
Stage #2: With hydrogenchloride In water at 0℃;
A mixture of (S)-2-azetidinecarboxyic acid (1Og, 98.9mmol), di-tert butyl dicarbonate (28.06g, 128.6mmol), N-methyl morpholine (11.5g, 113.7mmol), 1,4-dioxane (160ml) and water (160ml) was stirred at O0C for 4 hours and then at ambient temperature for 18 hours. The volatiles were removed by evaporation and the residue was dissolved in water, washed with DCM and the aqueous layer acidified to pH 1.0 at O0C with concentrated hydrochloric acid. The aqueous layer was extracted with DCM and the organic layer dried (Na2SO4) over anhydrous sodium sulfate to give iV-tert-butyloxycarbonylazetidin-2-yl carboxylic acid (12.61g, 63.1percent) as an oil; NMR Spectrum (CDCl3) 1.42 (s, 9H), 2.40 (m, IH), 2.59 (m, IH), 3.90 (m, 2H), 4.80 (t, IH).
Reference: [1] Patent: WO2006/100461, 2006, A1, . Location in patent: Page/Page column 79
[2] Patent: US5409946, 1995, A,
  • 2
  • [ 24424-99-5 ]
  • [ 2517-04-6 ]
  • [ 159749-28-7 ]
Reference: [1] Journal of Medicinal Chemistry, 2017, vol. 60, # 9, p. 3703 - 3726
[2] Patent: US5612360, 1997, A,
[3] Patent: US5646165, 1997, A,
[4] Patent: US5681844, 1997, A,
[5] Patent: US5739104, 1998, A,
[6] Patent: WO2012/162635, 2012, A1, . Location in patent: Page/Page column 118
[7] Patent: EP2697246, 2018, B1, . Location in patent: Paragraph 0284
[8] Patent: US5556981, 1996, A,
[9] Patent: US5658939, 1997, A,
  • 3
  • [ 255882-72-5 ]
  • [ 159749-28-7 ]
Reference: [1] Patent: WO2011/44506, 2011, A2, . Location in patent: Page/Page column 211
  • 4
  • [ 24424-99-5 ]
  • [ 159749-28-7 ]
YieldReaction ConditionsOperation in experiment
2.5 g
Stage #1: With hydrogen; palladium(II) hydroxide In methanol at 50℃; for 7 h;
Stage #2: With sodium hydroxide In methanol at 20℃;
Stage #3: With hydrogenchloride In methanol; water
A mixture of 12a (3.70 g, 13.2 mmol), Di-tert butyl dicarbonate (5.70 g, 26.3 mmol), and Pd(OH)2 (0.90 g, 6.43 mmol) in MeOH (100 mL) was stirred under H2 atmosphere at 50°C for 7 hours. The reaction mixture was cooled to room temperature and filtered. The filtrate was treated with 2 N NaOH (40 mL) and stirred at room temperature overnight. The reaction mixture was concentrated under reduced pressure. The residue was extracted with EtOAc (50 mL). The liquid phase was acified with 1 N HC1, adjusted pH=2 and extracted with DCM:i- PrOH = 4: 1 (150 mL x 3). The combined organic layers was washed with water (100 mL), dried over Na2S04 and concentrated under reduced pressure to give the title compound 12b (2.50 g) as colorless oil. MS-ESI (m/z): 146.0 [M + 1 - 56]+.
Reference: [1] Patent: WO2015/7219, 2015, A1, . Location in patent: Page/Page column 37-38
  • 5
  • [ 24424-99-5 ]
  • [ 159749-28-7 ]
Reference: [1] Journal of the Chemical Society, Chemical Communications, 1994, # 7, p. 879 - 880
  • 6
  • [ 24424-99-5 ]
  • [ 159749-28-7 ]
Reference: [1] Polish Journal of Chemistry, 2006, vol. 80, # 2, p. 265 - 277
  • 7
  • [ 67-56-1 ]
  • [ 159749-28-7 ]
  • [ 255882-72-5 ]
YieldReaction ConditionsOperation in experiment
84%
Stage #1: With 4-methyl-morpholine; isobutyl chloroformate In tetrahydrofuran at -10 - 25℃; for 4 h;
Stage #2: at 18 - 25℃; for 18 h;
Isobutyl chloroformate (8.43 Ig, 61.7mmol) was added to a solution of iV-tert- butyloxycarbonylazetidin-2-yl carboxylic acid (12.42g, 61.7mmol) and N-methyl morpholine (6.23g, 61.7mmol) in anhydrous THF (20ml) cooled at -10°C under an nitrogen atmosphere, at such a rate to keep the reaction temperature below -8 0C. The reaction mixture was then stirred at -8 °C for 1 hour and then at ambient temperature for a further 3 hours. Methanol (200ml) was added and the reaction mixture stirred at ambient temperature for 18 hours. The volatiles were removed by evaporation and the residue partitioned between water and diethylether. The organic layer was separated, dried (Na2SO4) give methyl N-tert- butyloxycarbonylazetidin-2-yl carboxylate (11.15g, 84.0percent) as an oil; NMR Spectrum (CDCl3) 1.43 (s, 9H), 2.20 (m, IH), 2.50 (m, IH), 3.78 (s, 3H), 3.90 (m, IH), 4.00 (m, IH), 4.60 (m, IH).
Reference: [1] Patent: WO2006/100461, 2006, A1, . Location in patent: Page/Page column 79
  • 8
  • [ 159749-28-7 ]
  • [ 174346-82-8 ]
YieldReaction ConditionsOperation in experiment
1.25 g With dimethylsulfide borane complex In tetrahydrofuran at 0 - 20℃; for 3 h; To a solution of 12b (1.45 g, 7.21 mmol) in anhydrous THF (12 mL) was added dropwise Borane-methyl sulfide complex (10M, 3 mL) at 0 °C. The reaction mixture was warmed to room temperature for 3 hours. Then it was quenched with MeOH (10 mL), diluted with DCM (100 mL), washed with water (40 mL χ 3), dried over Na2S04 and concentrated under reduced pressure to give the title compound 12c (1.25 g) as colorless oil. MS-ESI (m/z): 132.0 [M + 1 - 56]+.
Reference: [1] Patent: WO2015/7219, 2015, A1, . Location in patent: Page/Page column 38
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