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CAS No. : | 497160-14-2 | MDL No. : | MFCD11559001 |
Formula : | C11H19NO4 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | OPTPWZDWKAOOPP-UHFFFAOYSA-N |
M.W : | 229.27 | Pubchem ID : | 53249565 |
Synonyms : |
|
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P280-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302 | 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 |
---|---|---|
92% | With lithium aluminium tetrahydride In tetrahydrofuran at -78 - 20℃; for 3 h; | tert-butyl azetidinecarboxylic acid methyl ester (2 g, 8.7 mmol) was dissolved in anhydrous tetrahydrofuran (150 mL), lithium aluminum hydride (497 mg) was added and the mixture was stirred at 78 ° C for 3 hours. The temperature of the obtained reaction mixture was raised to room temperature, sodium sulfate (4 g) was added, and the mixture was stirred for one day. The resulting reaction mixture was dried over anhydrous magnesium sulfate, filtered and washed with methylene chloride. The solvent of the reaction mixture was removed by evaporation under reduced pressure to obtain Compound 3 in a liquid state. This product was identified as a single compound by TLC (n-hexane: ethyl acetate (1: 1, v / v)). |
85% | With lithium aluminium tetrahydride In tetrahydrofuran at 0℃; for 1 h; | Example 44: Synthesis of(2S,5R)-2-(5-(3-(az.etidin-3-yl)propyl)-l,3,4-oxadiaz.ol-2-yl)-7-oxo- l,6-diazabicyclo[3.2.1 loctan-6-yl hydrogen sulfate (Compound 743) ESI-MS (EI+, m/z): 388.2. 1H NMR (300 MHz, D20) δ 4.75 (d, / = 6.5 Hz, 1H), 4.16 (br s, 1H), 4.11 - 3.99 (m, 2H), 3.72 (dd, / = 11.4, 7.6 Hz, 2H), 3.22 - 3.10 (m, 1H), 2.95 - 2.74 (m, 4H), 2.34 - 2.03 (m, 3H), 2.01 - 1.77 (m, 1H), 1.72 - 1.50 (m, 4H). |
80% | With lithium aluminium tetrahydride In tetrahydrofuran at 0℃; for 0.5 h; | Example 21: Synthesis of(2S,5R)-2-(5-(az.etidin-3-ylmethyl)isoxaz.ol-3-yl)-7-oxo-l,6- diazabicyclo[3.2.1 loctan-6-yl hydrogen sulfate (Compound 618, ) Synthetic scheme: Characterization: (2S,5R)-2-(5-(azetidin-3-ylmethyl)isoxazol-3-yl)-7-oxo-l ,6-diazabicyclo[3.2.1]octan-6-yl hydrogen sulfate (618, 75 mg) was obtained as a white solid after prep-HPLC purification using ammonium formate buffer. ESI-MS (EI+, m/z): 359.0. 1H NMR (300 MHz, D20) δ 6.23 (s, 1H), 4.56 (d, / = 6.6 Hz, 1H), 4.15 - 4.08 (m, 2H), 3.93 - 3.82 (m, 2H), 3.44 (dd, / = 14.3, 7.2 Hz, 1H), 3.28 (dt, / = 15.9, 7.9 Hz, 1H), 3.10 - 3.03 (m, 3H), 2.87 (d, / = 12.1 Hz, 1H), 2.21 - 1.94 (m, 3H), 1.84 - 1.76 (m, 1H). |
103 mg | Stage #1: With diisobutylaluminium hydride In tetrahydrofuran at -78 - 0℃; for 2 h; Stage #2: With water In tetrahydrofuran |
To a mixture of tert-butyl 3-(2-methoxy-2-oxo-ethyl)azetidine-l-carboxylate (200.00 mg, 872.33 umol, 1.00 eq) in THF (10.00 mL) was added DIBAL-H (1 M, 2.62 mL, 3.00 eq) dropwise at -78 °C. The reaction mixture was stirred at 0 °C for 2h. Water (20 mL) was added and the mixture was extracted with EtOAc (15 mL *3). The organic layers were concentrated and the crude residue was purified by silica gel chromatography (Petroleum ether : Ethyl acetate=20: l to 1: 1) to afford tert-butyl 3-(2-hydroxyethyl)azetidine-l- carboxylate (103.00 mg). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
112 mg | With hydrogenchloride In methanol at 0 - 25℃; for 2 h; | To a solution of tert-butyl 3-(2-methoxy-2-oxo-ethyl)azetidine-l-carboxylate (200 mg, 872.33 umol, 1.00 eq) in MeOH (2 mL) was added HC1 (4 M in MeOH, 2 mL, 9.17 eq) at 0 °C .The mixture was stirred at 25 °C for 2 h. The mixture was concentrated to afford crude methyl 2-(azetidin-3-yl)acetate (112 mg, 867.14 umol). 1H NMR (400MHz, CD3OD) δ 4.16 (t, J=9.9 Hz, 2H), 3.95 - 3.87 (m, 2H), 3.73 - 3.65 (m, 3H), 3.28 - 3.19 (m, 1H), 2.78 - 2.69 (m, 2H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With trifluoroacetic acid; In dichloromethane; | A mixture of [1-(tert-butoxycarbonyl)azetidin-3-yl]acetic acid (2 g, 9.24 mmol), potassium carbonate (1.54 g, 11.1 mmol) and methyl iodide (2.89 mL, 46.5 mmol) in N,N-dimethylformamide (30 mL) was stirred at room temperature under nitrogen overnight. The reaction mixture was diluted with water and extracted with dichloromethane (x2). The combined organic layers were washed with saturated sodium hydrogencarbonate solution, dried over MgSO4 and concentrated in vacuo. The residue was dissolved in dichloromethane (5 mL) and trifluoroacetic acid (5 mL) added. The reaction was stirred at room temperature for 30 minutes. The solvent was removed in vacuo. The residue was dissolved in N,N-dimethylformamide (30 mL). 2,4-Difluorophenethyl bromide (2.26 g, 10.2 mmol) and potassium carbonate (5.14 g, 37.2 mmol) were added and the reaction heated at 60° C. overnight. The cooled reaction mixture was diluted with water and extracted with dichloromethane (x3). The combined organic layers were washed with brine, dried over MgSO4 and concentrated in vacuo. The residue was purified by flash column chromatography on silica, eluding with 5percent methanol/dichloromethane, to give methyl{1-[2-(2,4-difluorophenyl)ethyl]azetidin-3-yl}acetate (1.3 g, 52percent). 1H NMR (360 MHz, CDCl3) delta 7.15-7.09 (1H, m), 6.79-6.71 (2H, m), 3.64 (3H, s), 3.48-3.44 (2H, m), 2.87-2.75 (3H, m), 2.60 (4H, s), 2.57 (2H, d, J=7.1 Hz); m/z (ES+) 270 (M+H)+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
96% | With hydrazine hydrate; In methanol; at 20 - 65℃; for 12.0h; | diazabicyclo[3.2.1 loctan-6-yl hydrogen sulfate (Compound 725) Step 1: Synthesis of tert-butyl 3-(2-hydrazinyl-2-oxoethyl)azetidine-l -carboxylate: To a solution of teri-butyl 3-(2-methoxy-2-oxoethyl)azetidine-l-carboxylate (25.0 g, 109 mmol) in MeOH (150 mL) was added NuEta2NuEta220 (27.3 g, 546 mmol) at rt. The mixture was heated at 65 °C for 12 hrs and then concentrated. The residue was diluted with DCM (400 mL), washed with water (2x) and saturated sodium chloride (2x), dried over Na2S04, and concentrated to give ieri-butyl 3-(2-hydrazinyl-2-oxoethyl)azetidine-l-carboxylate (24.0 g, 96percent) as a yellow gum. ESI-MS (EI+, m/z): 252 [M+Na]+. Step 2: Synthesis of 'tert-butyl 3-(2-(2-((2S,5R)-6-(benzyloxy)-7-oxo-l,6-diaza bicyclo[3.2. l]octane-2-carbonyl)hydrazinyl)-2-oxoethyl)azetidine-l -carboxylate: HATU (19.6 g, 52.2 mmol) and DIPEA (16.6 g, 130.5 mmol) were added to a 0 °C solution of (25',5 ?)-6-(benzyloxy)-7-oxo-l,6-diaza-bicyclo[3.2.1]octane-2-carboxylic acid (12.0 g, 43.5 mmol), ieri-butyl 3-(2-hydrazinyl-2-oxoethyl)azetidine-l-carboxylate(11.3 g, 49.8 mmol) in CH2C12 (360 mL). The mixture was allowed to warm to rt then the mixture was stirred at rt for 12 hrs. The mixture was then diluted with CH2C12 (300 mL), washed with water (2x)and saturated sodium chloride(2x), dried and concentrated. The residue was purified by silica gel column chromatography (0-20percent gradient elution EtOAc/petroleum ether) to afford ieri-butyl 3-(2-(2-((25',5)-6-(benzyloxy)-7-oxo-l,6-diaza bicyclo[3.2.1 ]octane-2-carbonyl)hydrazinyl)-2-oxoethyl)azetidine- 1 -carboxylate ( 19.3 g, 93percent) as a white solid. ESI-MS (EI+, m/z): 488 [M+H]+. Step 3: Synthesis of tert-butyl 3 -((5-((2S, 5R)-6-(benzyloxy )-7-oxo-l, 6-diaza- bicyclo[3.2. l]octan-2-yl)-l, 3, 4-oxadiazol-2-yl)methyl)azetidine-l -carboxylate: To s solution of PPh3 (2.2 g, 8.2 mmol) in dry DCM (60 mL) was added I2 (2.1 g, 8.2 mmol). After I2 was dissolved completely, TEA (1.7 g, 16.4 mmol) was added quickly at rt. The mixture was stirred for 15 mins. 7ri-butyl 3-(2-(2-((25',5 ?)-6-(benzyloxy)-7-oxo-l ,6-diaza bicyclo[3.2.1]octane-2-carbonyl)hydrazinyl)-2-oxoethyl)azetidine-l-carboxylate (2.0 g, 4.1 mmol) was added. The mixture was stirred at rt for 1 h. The reaction mixture was concentrated and the residue was purified by silica gel column chromatography (gradient elution 0-40percent EtOAc/petroleum ether) to afford ieri-butyl 3-((5-((2S,5fl)-6-(benzyloxy)-7- oxo- l,6-diaza-bicyclo[3.2.1]octan-2-yl)-l ,3,4-oxadiazol-2-yl)methyl)azetidine-l-carboxylate (1.3 g, 66percent) as a white solid. ESI-MS (EI+, m/z): 470 [M+H]+. Step 4-6: Following Steps 3-5 in Example 4, replacing ieri-butyl (2-(5-((2S,5R)-6- (benzyloxy)-7-oxo-l,6-diazabicyclo[3.2.1]octan-2-yl)-l ,3,4-oxadiazol-2-yl)ethyl)carbamate in Step 3 with ieri-butyl 3-((5-((2S,5R)-6-(benzyloxy)-7-oxo-l,6-diazabicyclo[3.2.1]octan-2- yl)-l,3,4-oxadiazol-2-yl)methyl)azetidine-l -carboxylate, (2S,5R)-2-(5-(azetidin-3-ylmethyl)- l,3,4-oxadiazol-2-yl)-7-oxo-l,6-diazabicyclo[3.2.1]octan-6-yl hydrogen sulfate was obtained as a white solid after prep-HPLC purification using ammonium formate buffer. ESI-MS (EI+, m/z): 360.2. 1H NMR (300 MHz, D20) 4.74 (d, / = 6.4 Hz, 1H), delta 4.23 - 4.15 (m, 3H), 3.95 (dd, / = 11.5, 7.5 Hz, 2H), 3.50 - 3.30 (m, 1H), 3.25 (d, / = 6.0 Hz, 2H), 3.17 - 3.14 (m, 1H), 2.88 (d, / = 12.0 Hz, 1H), 2.27 - 2.05 (m, 3H), 1.95-1.85 (m, 1H). |
Tags: 497160-14-2 synthesis path| 497160-14-2 SDS| 497160-14-2 COA| 497160-14-2 purity| 497160-14-2 application| 497160-14-2 NMR| 497160-14-2 COA| 497160-14-2 structure
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