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[ CAS No. 105258-93-3 ] {[proInfo.proName]}

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Chemical Structure| 105258-93-3
Chemical Structure| 105258-93-3
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Product Details of [ 105258-93-3 ]

CAS No. :105258-93-3 MDL No. :MFCD09954923
Formula : C11H11NO3 Boiling Point : -
Linear Structure Formula :- InChI Key :VLMMTGKGDOAYER-UHFFFAOYSA-N
M.W : 205.21 Pubchem ID :10632047
Synonyms :

Calculated chemistry of [ 105258-93-3 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 15
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.27
Num. rotatable bonds : 4
Num. H-bond acceptors : 3.0
Num. H-bond donors : 0.0
Molar Refractivity : 57.21
TPSA : 46.61 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.65 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.1
Log Po/w (XLOGP3) : 1.27
Log Po/w (WLOGP) : 0.68
Log Po/w (MLOGP) : 0.77
Log Po/w (SILICOS-IT) : 1.47
Consensus Log Po/w : 1.26

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.94
Solubility : 2.33 mg/ml ; 0.0114 mol/l
Class : Very soluble
Log S (Ali) : -1.85
Solubility : 2.91 mg/ml ; 0.0142 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.55
Solubility : 0.576 mg/ml ; 0.00281 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.87

Safety of [ 105258-93-3 ]

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 [ 105258-93-3 ]

* 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 [ 105258-93-3 ]
  • Downstream synthetic route of [ 105258-93-3 ]

[ 105258-93-3 ] Synthesis Path-Upstream   1~6

  • 1
  • [ 128117-22-6 ]
  • [ 105258-93-3 ]
YieldReaction ConditionsOperation in experiment
99% With Dess-Martin periodane In dichloromethane at 20℃; for 5 h; To a solution of phenylmethyl 3-hydroxyazetidine-l-carboxylate (3.5 g, 0.0168 mol) in dichloromethane (100 mL) was added Dess-Martin periodinane (10.7 g, 0.0.25 mol) at room temperature and stirred for 5 h. The reaction mixture was quenched with 1 :1 ratio of saturated aqueous sodium bicarbonate and IM sodium thiosulfate (200 mL) and then partitioned with dichloromethane. The organic layer was dried over anhydrous magnesium sulfate and concentrated in vacuo to afford phenylmethyl 3-oxoazetidine-l-carboxylate (3.43 g, 99percent yield) as a clear and colorless oil without further purification. 1H NMR (400 MHz, CDCl3): 7.39-7.31 (m, 5H), 5.17 (s, 2H), 4.77 (s, 4H). MS (EI) for Ci1H11NO3: 205 (M+).
99% With Dess-Martin periodane In dichloromethane at 20℃; for 5 h; To a solution of phenylmethyl 3-hydroxyazetidine-l-carboxylate (3.5 g, 0.0168 mol) in dichloromethane (100 mL) was added Dess-Martin periodinane (10.7 g, 0.0.25 mol) at room temperature and stirred for 5 h. The reaction mixture was quenched with 1:1 ratio of saturated aqueous sodium bicarbonate and IM sodium thiosulfate (200 mL) and then partitioned with dichloromethane. The organic layer was dried over anhydrous magnesium sulfate and concentrated in vacuo to afford phenylmethyl 3-oxoazetidine-l-carboxylate (3.43 g, 99percent yield) as a clear and colorless oil without further purification. 1H NMR (400 MHz, CDCl3): 7.39-7.31 (m, 5H), 5.17 (s, 2H), 4.77 (s, 4H). MS (EI) for Ci 1HnNO3: 205 (M+).
99% With Dess-Martin periodane In dichloromethane at 20℃; for 5 h; To a solution of phenylmethyl 3-hydroxyazetidine-l-carboxylate (3.5 g, 0.0168 mol) in dichloromethane (100 mL) was added Dess-Martin periodinane (10.7 g, 0.0.25 mol) at room temperature and stirred for 5 h. The reaction mixture was quenched with 1 : 1 ratio of saturated aqueous sodium bicarbonate and IM sodium thiosulfate (200 mL) and then partitioned with dichloromethane. The organic layer was dried over anhydrous magnesium sulfate and concentrated in vacuo to afford phenylmethyl 3-oxoazetidine-l-carboxylate (3.43 g, 99percent yield) as a clear and colorless oil without further purification. 1H NMR (400 MHz, CDCl3): 7.39-7.31 (m, 5H), 5.17 (s, 2H), 4.77 (s, 4H). MS (EI) for CnHnNO3: 205 (M+).
48% With sulfur trioxide pyridine complex; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine In dichloromethane at 0℃; for 1 h; To a stirred solution of intermediate 1 -1 (13.60 g, 66 mmol) in DCM (100 mL) at 0°C was added DIPEA (57.5 mL 0.33 mol) dropwise, followed by pyridine sulfur trioxide (24.20 g, 0.15 mol) in DMSO (70 mL). The resulting mixture was stirred at 0°C for 1 h. The mixture was then poured into ice-water and the aqueous layer extracted twice with DCM. The combined organic layers were washed with brine and dried (Na2S04), filtered and concentrated. The crude product was purified by column chromatography (EtOAc/Pet. ether 1 :2) to obtaincompound 1-2 (6.50 g 48percent) as yellow solid. The structure was confirmed by H-N R spectra. TLC:Rf=0.7(silica gel,EA:PE=1 : 1 , v/v). 1H-NMR(400MHz,CDCI3)5(ppm):7.38 (m, 5H),5.17 (s, 2H),4.76 (s, 4H).
17.9 g With pyridine-SO3 complex; triethylamine In dimethyl sulfoxide at 0 - 20℃; for 16.3333 h; A solution of the sub-title product of step (i) (17.9 g) in DMSO (100 mL) was added drop wise over 15 minutes to a solution of pyridine sulphur trioxide (44.7 g) and triethylamine (39.3 mL) in DMSO (200 ml) at 0 °C (slight exotherm to 5C). The mixture was warmed to RT after 5 minutes and stirred for 16 hours. The mixture was poured into ice/water and extracted twice with ethyl acetate. The combined organics were washed with brine, dried over sodium sulfate and concentrated in vacuo to give crude product. The crude product was purified by flash silica chromatography, elution 100percent dichloromethane. Pure fractions were evaporated to dryness to afford the sub-title product (17.9 g) as a pale yellow oil. 1H NMR (500 MHz, CDCL3) δ 7.40 - 7.31 (m, 5H), 5.17 (s, 2H), 4.78 (s, 4H).
17.9 g With sulfur trioxide pyridine complex; triethylamine In dimethyl sulfoxide at 0 - 20℃; for 16.3333 h; A solution of the sub-title product of step (i) (17.9 g) in DMSO (100 mL) was added drop wise over 15 minutes to a solution of pyridine sulphur trioxide (44.7 g) and triethylamine (39.3 mL) in DMSO (200 ml) at 0 °C (slight exotherm to 5C). The mixture was warmed to RT after 5 minutes and stirred for 16 hours. The mixture was poured into ice/water and extracted twice with ethyl acetate. The combined organics were washed with brine, dried over sodium sulfate and concentrated in vacuo to give crude product. The crude product was purified by flash silica chromatography, elution 100percent dichloromethane. Pure fractions were evaporated to dryness to afford the sub-title product (17.9 g) as a pale yellow oil. 1H NMR (500 MHz, CDCL3) δ 7.40 - 7.31 (m, 5H), 5.17 (s, 2H), 4.78 (s, 4H).

Reference: [1] Patent: WO2007/44515, 2007, A1, . Location in patent: Page/Page column 165
[2] Patent: WO2008/76415, 2008, A1, . Location in patent: Page/Page column 329
[3] Patent: WO2008/124085, 2008, A2, . Location in patent: Page/Page column 179
[4] Patent: WO2014/32, 2014, A1, . Location in patent: Page/Page column 33; 34
[5] Patent: WO2013/8002, 2013, A1, . Location in patent: Page/Page column 49
[6] Patent: EP2740458, 2016, B1, . Location in patent: Paragraph 0052
  • 2
  • [ 40320-60-3 ]
  • [ 501-53-1 ]
  • [ 105258-93-3 ]
Reference: [1] Heterocycles, 1986, vol. 24, # 1, p. 25 - 28
[2] Patent: EP1757582, 2007, A1, . Location in patent: Page/Page column 34-35
  • 3
  • [ 67865-70-7 ]
  • [ 105258-93-3 ]
Reference: [1] Journal of the Chemical Society - Perkin Transactions 1, 1999, # 16, p. 2277 - 2280
[2] Journal of Organic Chemistry, 2002, vol. 67, # 5, p. 1536 - 1547
  • 4
  • [ 55378-79-5 ]
  • [ 105258-93-3 ]
Reference: [1] Journal of Organic Chemistry, 2002, vol. 67, # 5, p. 1536 - 1547
  • 5
  • [ 501-53-1 ]
  • [ 105258-93-3 ]
Reference: [1] Patent: WO2013/8002, 2013, A1,
[2] Patent: WO2014/32, 2014, A1,
[3] Patent: EP2740458, 2016, B1,
  • 6
  • [ 1138-80-3 ]
  • [ 105258-93-3 ]
Reference: [1] Journal of the Chemical Society - Perkin Transactions 1, 1999, # 16, p. 2277 - 2280
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