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CAS No. : | 18621-18-6 | MDL No. : | MFCD02683887 |
Formula : | C3H8ClNO | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | UQUPQEUNHVVNKW-UHFFFAOYSA-N |
M.W : | 109.55 | Pubchem ID : | 2759290 |
Synonyms : |
Azetidin-3-ol hydrochloride
|
Num. heavy atoms : | 6 |
Num. arom. heavy atoms : | 0 |
Fraction Csp3 : | 1.0 |
Num. rotatable bonds : | 0 |
Num. H-bond acceptors : | 2.0 |
Num. H-bond donors : | 2.0 |
Molar Refractivity : | 29.26 |
TPSA : | 32.26 Ų |
GI absorption : | High |
BBB permeant : | No |
P-gp substrate : | No |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | Yes |
Log Kp (skin permeation) : | -7.15 cm/s |
Log Po/w (iLOGP) : | 0.0 |
Log Po/w (XLOGP3) : | -0.25 |
Log Po/w (WLOGP) : | -0.63 |
Log Po/w (MLOGP) : | -0.57 |
Log Po/w (SILICOS-IT) : | 0.32 |
Consensus Log Po/w : | -0.23 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 2.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -0.36 |
Solubility : | 47.6 mg/ml ; 0.435 mol/l |
Class : | Very soluble |
Log S (Ali) : | 0.03 |
Solubility : | 118.0 mg/ml ; 1.07 mol/l |
Class : | Highly soluble |
Log S (SILICOS-IT) : | 0.18 |
Solubility : | 166.0 mg/ml ; 1.52 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.0 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P280-P305+P351+P338-P310 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H332-H335 | 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 |
---|---|---|
94% | With hydrogen In ethanol at 20℃; for 12 h; | A solution of l-(diphenylmethyl)-3-hydroxyazetidine hydrochloride (11.8 g) in absolute ethanol (700 mL) was hydrogenated at room temperature over Pd(OH)2/C in a Parr shaker at 4 atm. After 12 hr the catalyst was filtered off and the filtrate evaporated to dryness to give3-hydroxyazetidine hydrochloride (4.20 g, 94percent). 1H-NMR (300 MHz, DMSO-de, ppm from TMS): δ 9.07 (2H, bb), 6.19 (IH, bb), 4.49 (IH, m), 3.99 (2H, m), 3.71 (2H, m). |
52% | With hydrogen In methanol for 48 h; | A reaction mixture of N-benzhydrylazetidin-3-ol HCl salt (2.76 g, 10.0 mmol) with palladium hydroxide, 20percent Pd (dry base) on C (400 mg) in 50 mL of MeOH was hydrogenated at 55 psi for 48 h. The reaction mixture was filtered through Celite pad and washed well with MeOH. The filtrate was concentrated under vacuum at room temperature water bath. The residue was treated with ether (3x30 ml) and the solvent is decanted. The solid was air dried to give 571 mg of HCl salt product (2) as white solid (52percent yield). 1H NMR (400 MHz, DMSO-D6) δ ppm 3.33 (s, 1H) 3.63-3.80 (m, 2H) 3.93-4.09 (m, 2H) 4.40-4.58 (m, 1H) 6.18 (d, J=6.32 Hz, 1H). |
52% | With hydrogen In methanol for 48 h; | A reaction mixture of N-benzhydrylazetidin-3-ol HCI salt (2.76 g, 10.0 mmol) with palladium hydroxide, 20percent Pd (dry base) on C (400 mg) in 50 mL of MeOH was hydrogenated at 55 psi for 48 h. The reaction mixture was filtered through Celite pad and washed well with MeOH. The filtrate was concentrated under vacuum at room temperature water bath. The residue was treated with ether (3x30ml) and the solvent is decanted. The solid was air dried to give 571 mg of HCI salt product (2-2) as white solid (52percent yield). 1H NMR (400 MHz, DMSO-D6) 5 ppm 3.33 (s, 1 H) 3.63 - 3.80 (m, 2 H) 3.93 -4.09 (m, 2 H) 4.40 - 4.58 (m, 1 H) 6.18 (d, J=6.32 Hz, 1 H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
68% | With hydrogen In 1,4-dioxane; methanol at 60℃; for 6 h; | To a soln of 1-benzhydrylazetan-3-ol (1.0 g, 4.16 mmol) in methanol (20 mL) were added 10percent Pd/C (1.0 g) and 4N HCl in 1,4-dioxane (2 mL). The mixture was flushed with Ar, and then stirred on Parr apparatus at 40 psi H2 for 6 h at 60°. The mixture was cooled to room temperature and filtered through celite. The filtrate was concentrated and the resulting solid was washed with diethyl ether to give the desired product 0.31 g (68percent). 1H NMR (MeOD-d4): δ 4.17 (m, 1H), 4.22 (m, 2H), 3.91 (m, 2H) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | Stage #1: With potassium carbonate In tetrahydrofuran; water at 20 - 25℃; for 0.5 h; Stage #2: at 0 - 25℃; |
To a solution of azetidin-3-ol hydrochloride 7 (25 g, 0.23 mol) in water (150 mL) and THF (300 mL) was added K2CO3 (63.1 g, 0.46 mol). The mixture was stirred for 30 min. at 20-25 0C. Then benzyl chloroformate (40.9 g, 0.24 mol) was added within 30 min. at 0-5 °C followed by stirring the mixture overnight at 20-25 0C. THF was removed on a rotavap at 30 0C / vacuum and the mixture was extracted with ethyl acetate (2 x 150 mL). The combined organic layer was washed with water (1 x 50 mL), dried over Na2SO4 and concentrated. The residue was purified by flash column chromatography on silica gel, eluting with ethyl acetate- heptanes 1 : 1 and 4: 1 to yield 8 as a clear oil (47.3 g, 100percent). IH NMR (300 MHz, CDCl3): δ 3.72 (IH, d, J= 6.2 Hz), 3.85 (2H, dd, J= 9.5, 4.4 Hz), 4.17 (2H, dd, J= 9.5, 6.7 Hz), 4.49-4.57 (IH, m), 5.06 (2H, s), 7.31-7.38 (5H, m); 13C NMR (75 MHz, CDCl3): δ 59.2, 61.6, 66.9, 127.9, 128.1, 128.5, 136.5, 156.6; IR: (film) 3406, 1686, 1438 cm-1 ; ES-HRMS m/z: (M+ + IH) calcd. for C iH14NO3 208.0968, found 208.0967 |
87% | Stage #1: With potassium carbonate In tetrahydrofuran; water at 20℃; for 0.5 h; Stage #2: at 0 - 20℃; |
[0802] A mixture of azetidin-3-ol hydrochloride (12 g, 109.53 mmol, 1.00 equiv), tetrahydrofuran (150 mL), water (70 mL), and potassium carbonate (30 g, 217.07 mmol, 2.00 equiv) was stirred for 30 mm at room temperature. This was followed by the addition of benzyl chloroformate (22 g, 128.96 mmol, 1.20 equiv) dropwise with stirring at 0°C in 30 mm. The resulting solution was stirred overnight at room temperature. The solids were filtered out and the solution was extracted with ethyl acetate, washed with brine, dried over anhydrous sodium sulfate, and concentrated under vacuum. The residue was purified by a silica gel colunm eluting with ethyl acetate/petroleum ether (1:2) to afford the title compound (20 g, 87percent) as light yellow oil. LCMS [M+H] 208; ‘HNMR (400 MHz, DMSO-d6) 7.39 - 7.30 (m, 5H), 5.70 - 5.69 (d, J = 5.2 Hz, 1H), 5.03 (s, 2H), 4.44 - 4.42 (m, 1H), 4.10 (m, 2H), 3.69 (m, 2H). |
72% | With sodium carbonate In tetrahydrofuran; water at 20℃; for 1 h; | To a stirred solution of intermediate A (10.00 g, 91 mmol,) in H20 and THF (200 mL) was added Na2C03 (19.5g 0.18 mol), followed by Cbz-CI (18.40 g, 0.1 1 moL). The resulting mixture was stirred at rt for 1 h. The reaction mixture was quenched by addition of 1 M aq HCI. The aqueous layer was extracted twice with CH2CI2 and 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 :4) to obtain compound 1 - 1 (13.60 g, 72percent) as a white solid. The structure was confirmed by LC- S spectra. TLC:Rf=0.3(silica gel,EA:PE=1 :2, v/v) LC-MS :[M+1]+=208; [M+Na]=230. |
53% | With sodium chloride; sodium hydroxide In tetrahydrofuran; water at 0 - 20℃; for 3.5 h; | Example 50 Synthesis of 2-[1-[(2R)-2-[(3-hydroxyazetidin-1-yl)carbonyloxy]-2-phenylethyl]-5-methyl-6-(1,3-oxazol-2-yl)-2,4-dioxo-1H,2H,3H,4H-thieno[2,3-d]pyrimidin-3-yl]-2-methylpropanoic acid (I-230) Synthesis of Compound 50.2. To a solution of azetidin-3-ol hydrochloride (2 g, 18.26 mmol, 1.00 equiv) and sodium hydroxide (1.53 g, 38.25 mmol, 2.10 equiv) in water (10 mL) and tetrahydrofuran (25 mL) was added Cbz-Cl (3.27 g, 19.17 mmol, 1.05 equiv) dropwise with stirring at 0° C. over 30 min. The resulting solution was stirred for 3 h at room temperature. The reaction was then quenched by the addition of 20 mL of water. The mixture was extracted with 3*30 mL of ethyl acetate and the organic layers combined. The resulting mixture was washed with 2*40 mL of sodium chloride (sat.). The mixture was dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1:1). Purification afforded 2.0 g (53percent) of benzyl 3-hydroxyazetidine-1-carboxylate (50.2) as a light yellow liquid. |
33% | With triethylamine In tetrahydrofuran; water at 20℃; for 16 h; | To a solution of azetidin-3-ol hydrochloride in tetrahydrofuran (90 mL) and water (10 mL) was added triethylamine (15 mL, 0.106 mol) followed by slow addition of benzyl chloroformate (8.0 mL, 0.056 mol) at room temperature. The reaction mixture was stirred at room termperature for 16 hours then partitioned with water and ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate and concentrated. The residue was purified by flash chromatography (SiO2, 25-50percent ethyl acetate in hexanes) to afford phenylmethyl 3-hydroxyazetidine-l-carboxylate (3.56 g, 33percent yield) as a clear and colorless oil. 1H NMR (400 MHz, CDCl3): 7.36-7.31 (m, 5H), 5.09 (s, 2H), 4.64-4.57 (m, IH), 4.22 (dd, 2H), 3.88 (dd, 2H), 2.61 (d, IH, J=4.0 Hz). MS (EI) for C11H13NO3: 208 (MH+). |
33% | With triethylamine In tetrahydrofuran; water at 20℃; for 16 h; | To a solution of azetidin-3-ol hydrochloride in tetrahydrofuran (90 mL) and water (10 mL) was added triethylamine (15 mL, 0.106 mol) followed by slow addition of benzyl chloroformate (8.0 mL, 0.056 mol) at room temperature. The reaction mixture was stirred at room termperature for 16 hours then partitioned with water and ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate and concentrated. The residue was purified by flash chromatography (SiO2, 25-50percent ethyl acetate in hexanes) to afford phenylmethyl 3- hydroxyazetidine-1-carboxylate (3.56 g, 33percent yield) as a clear and colorless oil. 1H NMR (400 MHz, CDCl3): 7.36-7.31 (m, 5H), 5.09 (s, 2H), 4.64-4.57 (m, IH), 4.22 (dd, 2H), 3.88 (dd, 2H), 2.61 (d, IH, J=4.0 Hz). MS (EI) for CnHi3NO3: 208 (MH+). |
33% | With triethylamine In tetrahydrofuran; water at 20℃; for 16 h; | To a solution of azetidin-3-ol hydrochloride in tetrahydrofuran (90 mL) and water (10 mL) was added triethylamine (15 mL, 0.106 mol) followed by slow addition of benzyl chloroformate (8.0 mL, 0.056 mol) at room temperature. The reaction mixture was stirred at room termperature for 16 hours then partitioned with water and ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate and concentrated. The residue was purified by flash chromatography (SiO2, 25-50percent ethyl acetate in hexanes) to afford phenylmethyl 3-hydroxyazetidine-l-carboxylate (3.56 g, 33percent yield) as a clear and colorless oil. 1H NMR (400 MHz, CDCl3): 7.36-7.31 (m, 5H), 5.09 (s, 2H), 4.64-4.57 (m, IH), 4.22 (dd, 2H), 3.88 (dd, 2H), 2.61 (d, IH, J=4.0 Hz). MS (EI) for Ci1H13NO3: 208 (MH+). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
93% | With triethylamine In methanol at 0 - 20℃; for 6 h; | To a solution of 3-hydroxyazetidine hydrochloride (2.20 g) and triethyl- amine (4.0 mL) in MeOH (20 mL) at 0° C, di-tert-butyl dicarbonate (3.12 g) was added. After stirring at room temperature for 6 h, the solvent was evaporated. The residue was diluted with CH2CI2, washed with water and the organic phase was evaporated to dryness to give tert-butyl 3-hydroxy-l-azetidinecarboxylate (3.22 g, 93percent) which was used without purification in the next step. 1H-NMR (300 MHz, DMSO- de, ppm from TMS): δ 5.62 (IH, d), 4.35 (IH, m), 3.96 (2H, m), 3.55 (2H, m), 1.35 (9H, s). |
88% | With triethylamine In dichloromethane at 20℃; | To a solution of azetidin-3-ol hydrochloride (2.00 g, 18.3 mmcl) in CH2CI2 (20 mL) was added TEA (5 mL) and (Boc)20 (4.80 g, 22.0 mmcl). The mixture was stirred at rt overnight. The reaction mixture was concentrated. The residue was dissolved in EtOAc (20 mL). The mixture was washed with water (20 mLx 2) and brine (20 mL), dried over Na2504 andconcentrated to give the title compound (2.80 g, yield 88percent) as yellow oil.D486 1H NMR (300 MHz, CDCI3): 6 4.58-4.56 (m, 1H), 4.17-4.11 (m, 2H), 3.82-3.77 (m, 2H), 2.51-2.49 (m, 1H), 1.43 (s, 9H). |
85% | With triethylamine In ethanol at 0 - 20℃; for 16 h; | To a stirred cold (0° C.) solution of 3-hydroxyazetidine hydrochloride (75 g, 0.68 mol) in ethanol (1300 mL) was added triethylamine (208 g/280 mL, 2.05 mol) followed by Boc2O (164 g, 0.75 mol). The resultant solution was stirred at ambient temperature for 16 hours. GC/MS analysis of the reaction mixture revealed complete reaction. Volatiles were removed in vacuo and the residue was diluted with EtOAc (1300 mL) and washed with 10percent citric acid (700 mL), water (700 mL) and brine (700 mL). The organics were dried over sodium sulfate filtered, and concentrated to give the desired product (100.8 g, 85percent yield). 1H NMR (CDCl3) δ 4.6 (m, 1H), 4.2 (m, 2H), 3.8 (m, 2H), 1.4 (s, 9H). |
85% | With triethylamine In ethanol at 20℃; for 16 h; | To a stirred cold (0°C) solution of 3-hydroxyazetidine hydrochloride (75 g, 0.68 mol) in ethanol (1300 mL) was added triethylamine (208g/280mL, 2.05mol) followed by B0C2O (164 g, 0.75 mol). The resultant solution was stirred at ambient temperature for 16 hours. GC/MS analysis of the reaction mixture revealed complete reaction. Volatiles were removed in vacuo and the residue was diluted with EtOAc (1300 mL) and washed with 10percent citric acid (700 mL), water (700 mL) and brine (700 mL). The organics were dried over sodium sulfate filtered, and concentrated to give the desired product (100.8 g, 85percent yield).1 H NMR (CDCI3) δ 4.6 (m, 1 H), 4.2 (m, 2 H), 3.8 (m, 2 H), 1.4 (s, 9 H). |
81% | With sodium hydrogencarbonate In 1,4-dioxane; water at 20℃; for 1 h; | A mixture of 3-azetidinol hydrochloride (10 g, 91 mmol), di-tert-butyl dicarbonate (18.8 g, 86.3 mmol) and sodium bicarbonate (15.3 g, 182 mmol) in dioxane:water (400 mL, 1 :1) was stirre'd at room temperature for 15 hours. The organic portion was removed in vacuo and the aqueous portion was extracted with ethyl acetate three times. The combined organic portion was washed with 5percent aqueous HCl5 water, brine, dried over sodium sulfate, filtered and concentrated in-vacuo to afford 12.8 g, 74 mmol (81percent) of 1,1-dimethylethyl 3- hydroxyazetidine-1-carboxylate as a colorless oil without further purification. H NMR (400 MHz, DMSO): 5.62 (d, IH), 4.40-4.33 (m, IH), 4.02-3.95 (m, 2H), 3.62-3.54 (m, 2H), 1.37 (s, 9H). GC/MS for C8Hi5NO3: 173. |
81% | With sodium hydrogencarbonate In 1,4-dioxane; water at 20℃; for 15 h; | A mixture of 3-azetidinol hydrochloride (10 g, 91 mmol), di-tert-buty\\ dicarbonate (18.8 g, 86.3 mmol) and sodium bicarbonate (15.3 g, 182 mmol) in <n="340"/>dioxane: water (400 mL, 1:1) was stirred at room temperature for 15 hours. The organic portion was removed in vacuo and the aqueous portion was extracted with ethyl acetate three times. The combined organic portion was washed with 5percent aqueous HCl, water, brine, dried over sodium sulfate, filtered and concentrated in- vacuo to afford 12.8 g, 74 mmol (81percent) of 1,1-dimethylethyl 3-hydroxyazetidine- 1-carboxylate as a colorless oil without further purification. 1H NMR (400 MHz, DMSO): 5.62 (d, IH), 4.40-4.33 (m, IH), 4.02-3.95 (m, 2H), 3.62-3.54 (m, 2H), 1.37 (s, 9H). GC/MS for C8Hi5NO3: 173. |
81% | With sodium hydrogencarbonate In 1,4-dioxane; water at 20℃; for 15 h; | A mixture of 3-azetidinol hydrochloride (10 g, 91 mmol), di-tert-butyl dicarbonate (18.8 g, 86.3 mmol) and sodium bicarbonate (15.3 g, 182 mmol) in dioxane:water (400 mL, 1 : 1) was stirred at room temperature for 15 hours. The organic portion was removed in vacuo and the aqueous portion was extracted with ethyl acetate three times. The combined organic portion was washed with 5percent aqueous HCl, water, brine, dried over sodium sulfate, filtered and concentrated in-vacuo to afford 12.8 g, 74 mmol (81percent) of 1,1-dimethylethyl 3- hydroxyazetidine-1-carboxylate as a colorless oil without further purification. 1H NMR (400 MHz, DMSO): 5.62 (d, IH), 4.40-4.33 (m, IH), 4.02-3.95 (m, 2H), 3.62-3.54 (m, 2H), 1.37 (s, 9H). GC/MS for C8Hi5NO3: 173. |
78% | With sodium hydrogencarbonate In tetrahydrofuran; water at 25 - 30℃; for 12 h; Large scale | 10 kg of 3-hydroxyazetidine hydrochloride was dissolved in 100 kg of water and 84 kg of sodium bicarbonate was added.Take 52kg di-tert-butyl dicarbonate in 10L tetrahydrofuran to make a solution,And slowly adding the solution to the reaction system,The reaction was performed at 25-30[deg.] C. for 12 h.After monitoring by TLC, the reaction was completed, filtered and separated.The aqueous phase was extracted three times with ethyl acetate.Combine the organic phase,The organic phase is washed once with saturated saline solution.Dry over anhydrous sodium sulfate, filter, and concentrate under reduced pressure to give an oil.The oil was dissolved in 50 L of petroleum ether.Cool down to -50°C and stir for 12hWhite solid precipitated, filtered,It was dried to give N-Boc-3-hydroxyazetidine (white solid, 15 kg, yield: 78percent). |
69% | With triethylamine In ethanol at 20℃; for 24 h; | Step A: tert-Butyl 3-hydroxy-azetidine- 1 -carboxylate To a suspension of 3-azetidinol hydrochloride (2.50 g, 22.8 mmol) in 33 mL of ethanol is added di-?-butyl dicarbonate (5.47 g, 25.10 mmol) and triethylamine (9.60 mL, 68.5 mmol) and the mixture is stirred at room temperature for 24 h. The solvents are removed in vacuo, and the residue is taken up in ethyl acetate, washed with 10percent citric acid, water, and brine. The orgainc phase is dried over magnesium sulfate, filtered and evaporated to dryness. The resulting white solid is purified on silica gel using hexanes ethyl acetate as the eluent to give the title compound (3.00 g, 69.0percent). 1H NMR (400 MHz) : 4.70 (br s, IH), 4.19 (m, 2H), 3.81 (m, 2H), 1.42 (s, 9H). |
52% | With diethylamine In ethanol at 0 - 20℃; | To a cold (0 C. bath) stirred solution of compound (2) (570 mg, 5.20 mmol) in 10 mL of EtOH was added Et3N (1.8 mL, 13.0 mmol) and di-tert-butyldicarbonate (1.702 g, 7.38 mmol). The resulting mixture of clear solution was stirred at room temperature overnight. The reaction mixture was concentrated by vacuum. The residue was portioned between EtOAc (200 mL) and 0.5N citric acid solution (30 mL; brine (30 mL). The organic layer was dried (Na2SO4), then concentrated by vacuum to give 899 mg (2-) as clear oil (52percent). 1H NMR (400 MHz, chloroform-D) δ ppm 1.42 (s, 9H) 3.78 (dd, J=9.47, 4.42 Hz, 2H) 4.13 (dd, J=9.35, 6.57 Hz, 2H) 4.49-4.63 (m, 1H). |
52% | With triethylamine In ethanol at 20℃; | To a cold (0°C bath) stirred solution of compound (2-2) (570 mg, 5.20 mmol) in 10mL of EtOH was added Et3N (1.8 mL, 13.0 mmol) and di-tert-butyldicarbonate (1.702 g, 7.38 mmol). The resulting mixture of clear solution was stirred at room temperature overnight. The reaction mixture was concentrated by vacuum. The residue was portioned between EtOAc (200mL) and 0.5N citric acid solution (30mL; brine (30mL). The organic layer was dried (Na2SO4), then concentrated by vacuum to give 899 mg (2-3) as clear oil (52percent). 1H NMR (400 MHz, chloroform-D) 6 ppm 1.42 (s, 9 H) 3.78 (dd, J=9.47, 4.42 Hz, 2 H) 4.13 (dd, J=9.35, 6.57 Hz, 2 H) 4.49 -4.63 (m, 1 H). |
3.5 g | With sodium hydroxide In water at 0 - 35℃; | Cold aqueous NaOH (3.65 g, 91.25 mmol in 25 mL of water) was added to cold (0° C.) solution of azetidin-3-ol hydrochloride (4 g, 36.5 mmol) in water (15 mL) followed by addition of di-tert-butyl dicarbonate (8.4 mL, 38.33 mmol). The reaction mixture was stirred continuously at 20-35° C. for 12-14 h. The reaction mixture was diluted with ethyl acetate; the organic layer was separated, washed with water followed by brine solution, dried over anhydrous sodium sulphate and concentrated under reduce pressure to afford the crude compound, which was purified by column chromatography (using 60-120 silica gel and 30percent EtOAc in Hexane as eluent) to afford 3.5 g of the title compound. 1H NMR (400 MHz, DMSO) δ ppm 5.6 (1H, s), 4.4 (1H, bs), 4.0 (2H, t), 3.6-3.5 (2H, m), 1.4 (9H, s). |
17 g | Stage #1: With triethylamine In methanol at -10℃; for 2.5 h; Stage #2: at -10℃; |
SM2 (10.9 g, 0.1 mol) was dissolved in 200 mL of MeOH,-10 stirring reaction 30mins,After TEA (30.3 g, 0.3 mol) was added, the reaction was carried out for 2 h,(Boc) 2O (21.8 g, 0.1 mol) was added.The reaction was stirred at -10 ° C overnight.The organic phase was washed with brine, dried over anhydrous Na2SO4, filtered and concentrated to give the crude intermediate 664602 (17 g, 98percent), which was recrystallized from water and dried over anhydrous magnesium sulfate. |
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