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[ CAS No. 429669-07-8 ] {[proInfo.proName]}

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Chemical Structure| 429669-07-8
Chemical Structure| 429669-07-8
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Product Details of [ 429669-07-8 ]

CAS No. :429669-07-8 MDL No. :MFCD08689580
Formula : C9H17NO3 Boiling Point : -
Linear Structure Formula :- InChI Key :ZENIBVFXWKRVMK-UHFFFAOYSA-N
M.W : 187.24 Pubchem ID :22243050
Synonyms :

Calculated chemistry of [ 429669-07-8 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 13
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.89
Num. rotatable bonds : 4
Num. H-bond acceptors : 3.0
Num. H-bond donors : 0.0
Molar Refractivity : 52.87
TPSA : 38.77 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) : -6.87 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.68
Log Po/w (XLOGP3) : 0.8
Log Po/w (WLOGP) : 0.87
Log Po/w (MLOGP) : 0.56
Log Po/w (SILICOS-IT) : 0.51
Consensus Log Po/w : 1.08

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.24
Solubility : 10.8 mg/ml ; 0.0574 mol/l
Class : Very soluble
Log S (Ali) : -1.2
Solubility : 11.9 mg/ml ; 0.0637 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -0.84
Solubility : 26.8 mg/ml ; 0.143 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.31

Safety of [ 429669-07-8 ]

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

Application In Synthesis of [ 429669-07-8 ]

* 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 [ 429669-07-8 ]
  • Downstream synthetic route of [ 429669-07-8 ]

[ 429669-07-8 ] Synthesis Path-Upstream   1~4

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YieldReaction ConditionsOperation in experiment
93% With sodium hydride In tetrahydrofuran; mineral oil at 0 - 20℃; To a solution of 3-hydroxy-azetidine-1 -carboxylic acid tert-butyl ester (0.8 g, 4.62 mmol) in THF (50 mL) was added sodium hydride (60percent in mineral oil) (0.74 g, 18.5 mmol). The solution was stirred at 0 °C for 0.5 hour, followed by addition of iodomethane (2.8 mL, 46.2 mmol). The reaction mixture was stirred at room temperature overnight. The reaction was quenched with water (50 ml), and extracted with EtOAc (30 mL χ 3). The combined organic phases were dried over Na2S04, filtered and concentrated in vacuo to afford compound A9-1 (0.8 g, 93percent) as an oil. 1H NMR (400 MHz, CDCI3): δ 4.1 1 -4.13 (m, 1 H), 4.04-4.08 (m, 2 H), 3.79-3.83 (m, 2 H), 3.27 (s, 3 H), 1.43 (s, 9 H).
81%
Stage #1: With sodium hydride In DMF (N,N-dimethyl-formamide) at 0 - 20℃; for 0.666667 h;
Stage #2: at 0 - 20℃; for 1.16667 h;
(1) 1-t-Butoxycarbonyl-3-methoxyazetidine [1493] A solution of 1-benzhydryl-3-hydroxyazetidine (10.0 g, 41.8 mmol) in methanol (300 ml) was subjected to catalytic hydrogenation in the presence of 10percent palladium (10.0 g) on charcoal at room temperature for 3 hours. After checking the completion of the reaction, the reaction mixture was filtered in order to remove the catalyst. To the filtrate was added di-t-butoxycarbonic anhydride (18.2 g, 83.6 mmol), and the reaction mixture was stirred at room temperature for 1 hour. After checking the completion of the reaction, the reaction mixture was concentrated under reduced pressure. The residue was purified by chromatography on a silica gel column using n-hexane:ethyl acetate (1:1-->1:2) as the eluant to afford 1-t-butoxycarbonyl-3-hydroxyazetidine (7.05 g, yield 97percent). [1494] Subsequently, to a solution of 1-t-butoxycarbonyl-3-hydroxyazetidine (2.5 g, 14.4 mmol) in dimethylformamide (125 ml) was added sodium hydride (55percent oil dispersion) in an ice bath. After stirring the mixture for 10 minutes in the ice bath, the resulting mixture was stirred at room temperature for 30 minutes. To the reaction mixture was added methyl iodide (1.79 ml, 28. mmol) in an ice bath. After stirring the mixture in an ice bath for 10 minutes, the reaction mixture was stirred at room temperature for 1 hour. After checking the completion of the reaction, 10percent aqueous acetic acid solution was added thereto in an ice bath and the reaction mixture was stirred in the ice bath for 30 minutes. The reaction mixture was partitioned between ethyl acetate and 10percent aqueous sodium chloride solution. The organic layer was washed successively with saturated aqueous sodium hydrogencarbonate solution and saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by chromatography on a silica gel column using n-hexane:ethyl acetate (2:1) as the eluant to afford 1-t-butoxycarbonyl-3-methoxyazetidine (2.18 g, yield 81percent) as a colorless oil. [1495] 1H-NMR (400 MHz, CDCl3): δ (ppm) 4.16-4.10 (1H, m), 4.09-4.03 (2H, m), 3.82 (2H, dd, J=10.2, 4.4 Hz), 3.28 (3H, s), 1.44 (9H, s).
33.3% With sodium hydride In tetrahydrofuran at 0 - 20℃; for 3.25 h; A suspension of sodium hydride (2.89 g) in tetrahydrofuran (50 ml) was stirred with cooling in an ice bath. A solution of tert-butyl 3-hydroxyazetidine-1-carboxylate (5.00 g) in tetrahydrofuran (50 ml) was gradually added, followed by stirring at the same temperature for 30 minutes. Then, the reaction mixture was stirred at room temperature for 30 minutes. The reaction mixture was stirred with cooling in an ice bath again for 15 minutes. Iodomethane (3.09 ml) was added dropwise to the reaction mixture, followed by stirring for 2 hours. Water was gradually added to the reaction mixture. When bubbling stopped, the organic layer was separated. The aqueous layer was extracted with ethyl acetate. The organic layers were combined, washed with brine, and dried over anhydrous sodium sulfate. The solvent was distilled off, and the residue was purified by silica gel column chromatography (eluent; heptane:ethyl acetate=3:1, 2:1, 1:1, then ethyl acetate). The fractions containing the target compound were concentrated to give the title compound (1.80 g, 33.3percent) as a colorless oil. The fractions containing the starting material were concentrated and collected (2.10 g, 42.0percent).1H-NMR Spectrum (CDCl3) δ (ppm): 1.44 (9H, s), 3.28 (3H, s), 3.82 (2H, m), 4.06 (2H, m), 4.14 (1H, m).
Reference: [1] Organic Letters, 2014, vol. 16, # 3, p. 856 - 859
[2] Patent: WO2013/53690, 2013, A1, . Location in patent: Page/Page column 37; 38
[3] Patent: US2004/14962, 2004, A1, . Location in patent: Page/Page column 135
[4] Patent: US2008/214815, 2008, A1, . Location in patent: Page/Page column 16
[5] Patent: WO2011/63502, 2011, A1, . Location in patent: Page/Page column 50
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YieldReaction ConditionsOperation in experiment
33.3%
Stage #1: With sodium hydride In tetrahydrofuran at 0 - 20℃; for 1.25 h;
Stage #2: at 0℃; for 2 h;
(Production Example 92) tert-Butyl 3-methoxyazetidine-1-carboxylate
A suspension of sodium hydride (2.89 g) in tetrahydrofuran (50 ml) was stirred while cooling in an ice bath.
A solution of tert-butyl 3-hydroxyazetidine-1-carboxylate (5.00 g) in tetrahydrofuran (50 ml) was gradually added thereto, followed by stirring at the same temperature for 30 min.
Then, the reaction mixture was stirred at room temperature for 30 min.
The reaction mixture was again stirred while cooling in an ice bath for 15 min.
To the reaction mixture was added dropwise iodomethane (3.09 ml), followed by stirring for 2 hr.
Water was gradually added to the reaction mixture.
When bubbling stopped, the organic layer was separated.
The aqueous layer was extracted with ethyl acetate.
The organic layer was combined, washed with brine, and dried over anhydrous sodium sulfate.
The solvent was removed, and the residue was purified by silica gel column chromatography (eluent; heptane:ethyl acetate = 3:1, 2:1, 1:1, then ethyl acetate).
Fractions containing the target compound were concentrated to provide the titled compound as a colorless oil (1.80g, 33.3 percent).
Fractions containing the starting material were concentrated for recovery (2.10g, 42.0 percent).
1H-NMR Spectrum (CDCl3) δ (ppm): 1.44 (9H, s), 3.28 (3H, s), 3.82 (2H, m), 4.06 (2H, m), 4.14 (1H, m).
Reference: [1] Patent: EP1889836, 2008, A1, . Location in patent: Page/Page column 81
[2] Patent: WO2005/121110, 2005, A1, . Location in patent: Page/Page column 155
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Reference: [1] Organic Letters, 2018,
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Reference: [1] Patent: WO2011/63502, 2011, A1,
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