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CAS No. : | 870089-49-9 | MDL No. : | MFCD18073441 |
Formula : | C10H17NO3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | KRFZYPWUCOYOML-UHFFFAOYSA-N |
M.W : | 199.25 | Pubchem ID : | 59841137 |
Synonyms : |
|
Num. heavy atoms : | 14 |
Num. arom. heavy atoms : | 0 |
Fraction Csp3 : | 0.8 |
Num. rotatable bonds : | 4 |
Num. H-bond acceptors : | 3.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 56.79 |
TPSA : | 46.61 Ų |
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) : | -7.1 cm/s |
Log Po/w (iLOGP) : | 2.4 |
Log Po/w (XLOGP3) : | 0.58 |
Log Po/w (WLOGP) : | 1.06 |
Log Po/w (MLOGP) : | 0.76 |
Log Po/w (SILICOS-IT) : | 0.89 |
Consensus Log Po/w : | 1.14 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -1.18 |
Solubility : | 13.3 mg/ml ; 0.0666 mol/l |
Class : | Very soluble |
Log S (Ali) : | -1.13 |
Solubility : | 14.7 mg/ml ; 0.0738 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -1.06 |
Solubility : | 17.5 mg/ml ; 0.0879 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 2.05 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319 | Packing Group: | N/A |
GHS Pictogram: |
* 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.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
93% | Stage #1: at 0 - 20℃; for 3.66667 h; Stage #2: at 0℃; |
B. Preparation of tert-butyl 3-acetylazetidine-1-carboxylate (C56). A solution of C55 (27.1 g, 0.111 mol) in THF (200 mL) was added drop-wise to a 1.4M solution of methylmagnesium bromide in a mixture of THF and toluene (25:75) (99.0 mL, 0.139 mol) over 40 mins, while the reaction temp was kept at about 0° C. After completion of the addition, the mixture was stirred at 10-15° C. for 2 hours, followed by 1 h at room temp. The reaction mixture was cooled to 0° C. and quenched with a 10percent aqueous citric acid solution (150 mL). The organic layer was separated, and the aqueous layer was extracted with EtOAc (2*300 mL). The combined organic layers were washed with saturated aqueous sodium chloride solution (2*250 mL), and dried over sodium sulfate. Filtration and removal of solvent gave a residue, which was purified by silica gel chromatography (Eluant: chloroform) to afford C56. Yield: 20.6 g, 0.10 mol, 93percent. 1H NMR (400 MHz, CDCl3): δ 4.04-4.02 (m, 4H), 3.43-3.35 (m, 1H), 2.16 (s, 3H), 1.42 (s, 9H). |
93.4% | Stage #1: at 0 - 20℃; for 3.66667 h; Stage #2: With water; citric acid In tetrahydrofuran; toluene at 0℃; |
Preparation 85 tert-Butyl 3-acetylazetidine-1 -carboxylate; A solution of tert-butyl 3-(methoxy(methyl)carbamoyl)azetidine-1-carboxylate (Preparation 84, 27.1 g, 0.111 mol) in tetrahydrofuran (20OmL) was added dropwise to a 1.4 M solution of methylmagnesium bromide in a 25:75 mixture of tetrahydrofuran and toluene (99.0 mL, 0.139 mol, 1.25 eq) over 40 minutes. The reaction temperature was kept at ~0°C. After the addition, the mixture was stirred at 10-150C for 2 hours and then at room temperature for 1 hour. The mixture was cooled to 00C and 10percent aqueous citric acid (15OmL) was added. The organic layer was separated and the aqueous layer was extracted with ethyl acetate (60OmL). The organic layers were combined, washed with brine (50OmL) and dried using anhydrous sodium sulfate to give a residue which was purified by chromatography on silica gel, eluting with chloroform, to afford the title compound (20.6 g, 93.4percent).1H NMR (400 MHz, CDCI3): δ = 4.04-4.02 (m, 4H), 3.43-3.35 (m, 1 H), 2.16 (s, 3H), 1.42 (s, 9H) ppm. |
77% | at 0 - 20℃; for 17 h; | Methylmagnesium bromide (3M solution in THF, 10.4 mL, 31.3 mmol) was added dropwise to a cooled (0° C.) solution of tert-butyl 3-(methoxy(methyl)carbamoyl)azetidine-1-carboxylate (87a, 5.1 g, 20.88 mmol) in anhydrous THF (100 mL). Stirring was continued at 0° C. for one hour, then at room temperature for 16 hours. The mixture was cooled to 0° C. and quenched with sat. aq. NaHCO3 (35 mL), then extracted with ethyl acetate (3×40 mL). The combined organic extracts were washed with brine (3×40 mL), dried over sodium sulfate, filtered, concentrated, and purified by silica gel chromatography (eluting with petroleum ether/ethyl acetate from 10:1 to 3:1) to give tert-butyl 3-acetylazetidine-1-carboxylate (87b, (3.20 g, 77percent yield) as light yellow oil. 1H NMR (400 MHz, CDCl3) δ 4.05 (d, J=7.6 Hz, 4H), 3.41 (quint, J=7.6 Hz, 1H), 2.18 (s, 3H), 1.43 (s, 9H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | With acetic acid In 1,4-dioxane; water at 100 - 110℃; for 0.5 h; Microwave irradiation | Step 3: 3-Acetyl-azetidine-l-carboxylic acid tert- butyl esterA solution of 3-(2,2-dimethyl-4,6-dioxo-[l,3]dioxane-5-carbonyl)-azetidine-l- carboxylic acid terf-butyl ester (1.0 g, 3.05 mmol) in a mixture of actic acid (0.5 mL), water 0.25 mL and dioxane (3 mL) was stirred under microwaves at 100°C for 30 minutes. After concentration to dryness, the residue was coeveoparted with dichloromethane (2 x 100 mL). The title product was obtained as a colorless gum (600 mg, 100percent).LCMS (ESI-APCI) m/z 308.2 (M + H)+ |
70% | With acetic acid In 1,4-dioxane; water at 150℃; for 0.5 h; Microwave irradiation | To a stirring solution of compound 1 (2.8 g, 8.6 mmol) in dry dioxane (20 mL) was added AcOH (1.5 mL) and H20 (0.75 mL), then stirred at 150 °C for 30 mm with microwave heating.Quenched with water, extracted with EtOAc, concentrated under reduced pressure to obtain cmde product, which was purified by combiflash (methanol:DCM = 1:20) to give compound 2 (1.2 g, 70percent). LC-MS: m/z = 100.0 [M+H-Boc] |
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