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[ CAS No. 255882-72-5 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 255882-72-5
Chemical Structure| 255882-72-5
Chemical Structure| 255882-72-5
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Product Details of [ 255882-72-5 ]

CAS No. :255882-72-5 MDL No. :MFCD06657099
Formula : C10H17NO4 Boiling Point : -
Linear Structure Formula :- InChI Key :FGWUDHZVEBFGKS-UHFFFAOYSA-N
M.W : 215.25 Pubchem ID :14821735
Synonyms :

Calculated chemistry of [ 255882-72-5 ]

Physicochemical Properties

Num. heavy atoms : 15
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.8
Num. rotatable bonds : 5
Num. H-bond acceptors : 4.0
Num. H-bond donors : 0.0
Molar Refractivity : 57.88
TPSA : 55.84 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) : -6.76 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.79
Log Po/w (XLOGP3) : 1.2
Log Po/w (WLOGP) : 0.79
Log Po/w (MLOGP) : 0.74
Log Po/w (SILICOS-IT) : 0.47
Consensus Log Po/w : 1.2

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.6
Solubility : 5.4 mg/ml ; 0.0251 mol/l
Class : Very soluble
Log S (Ali) : -1.97
Solubility : 2.31 mg/ml ; 0.0107 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -0.8
Solubility : 34.2 mg/ml ; 0.159 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.8

Safety of [ 255882-72-5 ]

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 [ 255882-72-5 ]

* 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 [ 255882-72-5 ]
  • Downstream synthetic route of [ 255882-72-5 ]

[ 255882-72-5 ] Synthesis Path-Upstream   1~8

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  • [ 255882-72-5 ]
  • [ 159749-28-7 ]
Reference: [1] Patent: WO2011/44506, 2011, A2, . Location in patent: Page/Page column 211
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  • [ 67-56-1 ]
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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
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  • [ 1122-58-3 ]
  • [ 24424-99-5 ]
  • [ 69684-69-1 ]
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YieldReaction ConditionsOperation in experiment
87% With triethylamine In dichloromethane To a solution of azetidine-2(S)-carboxylic acid, methyl ester hydrochloride salt (6.6 mmol, 1.0 g) in anhydrous dichloromethane (14 mL) was added di-tert-butyl dicarbonate (1.05 equiv; 6.9 mmol, 1.51 g), triethylamine (3.0 equiv; 19.8 mmol, 2.0 g, 2.76 mL), and 4-dimethyl-aminopyridine in that order at 25° C.
Evolution of gas was observed almost immediately and the reaction mixture became cloudy.
After stirring overnight (15 h) it was diluted with ethyl acetate and washed with 1N hydrochloric acid, saturated bicarbonate solution, and brine.
Drying (MgSO4), filtration, and concentration afforded N-(tert-butyloxycarbonyl)-azetidine-2(S)-carboxylic acid, methyl ester as a pale yellow oil (1.24 g, 87percent yield) of satisfactory purity.
1H NMR (400 MHz, CDCl3): δ 4.63 (dd, 1H, J=9.2, 5.2 Hz), 4.05 (m, 1H), 3.89 (m, 1H), 3.79 (s, 3H), 2.51 (m, 1H), 2.18 (m, 1H), 1.43 (s, 9H).
Reference: [1] Patent: US6645939, 2003, B1,
  • 4
  • [ 24424-99-5 ]
  • [ 18085-37-5 ]
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Reference: [1] Organic Letters, 2006, vol. 8, # 19, p. 4335 - 4338
  • 5
  • [ 24424-99-5 ]
  • [ 134419-57-1 ]
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Reference: [1] Patent: US2003/229226, 2003, A1, . Location in patent: Page 19
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  • [ 543-27-1 ]
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Reference: [1] Patent: US5409946, 1995, A,
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  • [ 24424-99-5 ]
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Reference: [1] Patent: WO2006/100461, 2006, A1,
  • 8
  • [ 255882-72-5 ]
  • [ 174346-82-8 ]
Reference: [1] Patent: US2003/229226, 2003, A1, . Location in patent: Page 19
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