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[ CAS No. 152537-03-6 ]

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Chemical Structure| 152537-03-6
Chemical Structure| 152537-03-6
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CAS No. :152537-03-6 MDL No. :MFCD10699280
Formula : C10H19NO3 Boiling Point : 189-190°C at 760 mmHg
Linear Structure Formula :- InChI Key :N/A
M.W :201.26 g/mol Pubchem ID :22594530
Synonyms :

Safety of [ 152537-03-6 ]

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 [ 152537-03-6 ]

  • Upstream synthesis route of [ 152537-03-6 ]
  • Downstream synthetic route of [ 152537-03-6 ]

[ 152537-03-6 ] Synthesis Path-Upstream   1~6

  • 1
  • [ 183062-96-6 ]
  • [ 152537-03-6 ]
YieldReaction ConditionsOperation in experiment
100% With diborane In tetrahydrofuran at 0℃; for 1 h; 2-(1 -(tert-Butoxycarbonyl)azetidin-3-yl)acetic acid (3.91 g) was dissolved in THF (18.17 ml) and cooled to 0 °C. Diborane (1 M in THF, 54.5 ml) was added dropwise and the reaction stirred for one hour. Water was added dropwise to quench unreacted borane and the mixture diluted with EtOAc (150ml_) and washed with water (100ml_). Organics were dried over sodium sulphate and solvent evaporated under reduced pressure to afford tert-butyl 3-(2-hydroxyethyl)azetidine-1 -carboxylate (100 percent yield) as a clear oil.1H NMR (CDCI3)5: 4.0 (t, 2H), 3.60 (m, 4H), 2.65 (m, 1 H), 1 .85 (m, 2H), 1 .43 (s, 9H).
97%
Stage #1: With borane-THF In tetrahydrofuran at 0 - 20℃;
Stage #2: With sodium hydroxide In tetrahydrofuran; water
Intermediate 11 : 3-(2-Hydroxy-ethyl)-azetidine-1 -carboxylic acid tert-butyl ester. A solution consisting of S-carboxymethyl-azetidine-i -carboxylic acid tert-butyl ester (10.0 g, 46.5 mmol) and THF (15 ml_) was cooled to 0 0C and treated with a 1 M solution of borane in THF (70 ml_, 70 mmol), then slowly warmed to rt. After stirring for 18 h, the reaction mixture was quenched with 2 N NaOH (100 ml_), diluted with H2O (100 ml_), and extracted with Et2O (3x200 ml_). The organic layers were combined, dried (MgSO4), and concentrated to give the title compound as a colorless oil (9.03 g, 97percent). MS (ESI+): calcd. for C10H19NO3, 201.14; m/z found, 224.2 (M+Na)+. 1H NMR (d6-DMSO): 4.37 (t, J = 5.1 Hz, 1 H), 3.95-3.79 (m, 2H), 3.53-3.43 (m, 2H), 3.37 (dd, J = 11.5, 6.2 Hz, 2H), 2.62-2.52 (m, 1 H), 1.66 (dd, J = 13.8, 6.4 Hz, 2H), 1.39-1.33 (m, 9H).
94.15%
Stage #1: With borane-THF In tetrahydrofuran at -10 - 20℃;
Stage #2: With methanol In tetrahydrofuran at 0 - 20℃; for 0.5 h;
To a solution of 2-(1-(tert-butoxycarbonyl)azetidin-3-yl)acetic acid (7.5 g, 35mmol) in THF (100 mL) was added a solution of borane-tetrahydrofuran complex (105 mL,105 mmol, 1M in THF) dropwise at -10°C. The reaction was stirred at room temperatureovernight. To the reaction mixture was then added MeOH (50 mL) dropwise at 0°C. Afteraddition was complete, the mixture was stirred at room temperature for 30 mm. The mixturewas concentrated under vacuum to give a yellow reside, which was purified by silica gelcolumn chromatography (petroleum ether: EtOAc =100:1 to 1:1) to give tert-butyl 3-(2-hydroxyethyl)azetidine-1-carboxylate (6.6 g, 94.15percent yield) as a colorless oil. LC-MS mlz: 146 [M+H-56j.
Reference: [1] Patent: WO2011/86125, 2011, A1, . Location in patent: Page/Page column 61
[2] Patent: WO2010/141809, 2010, A1, . Location in patent: Page/Page column 33
[3] Patent: WO2017/27684, 2017, A1, . Location in patent: Paragraph 00148; 00254
[4] Patent: WO2018/140809, 2018, A1, . Location in patent: Paragraph 00454
  • 2
  • [ 497160-14-2 ]
  • [ 152537-03-6 ]
YieldReaction ConditionsOperation 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).

Reference: [1] Patent: KR101651994, 2016, B1, . Location in patent: Paragraph 0078-0080
[2] Patent: WO2013/149121, 2013, A1, . Location in patent: Page/Page column 120; 121
[3] Patent: WO2013/149136, 2013, A1, . Location in patent: Page/Page column 73; 74
[4] Patent: WO2016/172496, 2016, A1, . Location in patent: Paragraph 00788-00789
  • 3
  • [ 1378964-44-3 ]
  • [ 158602-35-8 ]
  • [ 24424-99-5 ]
  • [ 152537-03-6 ]
Reference: [1] Patent: US5648368, 1997, A,
  • 4
  • [ 158602-35-8 ]
  • [ 152537-03-6 ]
Reference: [1] Patent: US5281585, 1994, A,
  • 5
  • [ 288-32-4 ]
  • [ 152537-03-6 ]
  • [ 75-05-8 ]
  • [ 158602-36-9 ]
Reference: [1] Patent: US5281585, 1994, A,
  • 6
  • [ 152537-03-6 ]
  • [ 1420859-80-8 ]
YieldReaction ConditionsOperation in experiment
69.4% With carbon tetrabromide; triphenylphosphine In dichloromethane at 0 - 20℃; To a solution of tert-butyl 3-(2-hydroxyethyl)azetidine-1-carboxylate (6.1 g,30.3 mmol) was added a solution of CBr4 (19.8 g, 60.6 mmol) in DCM (100 mL) was addedPh3P (15.7 g, 60.6 mmol) at 0°C. The resulting mixture was stirred at room temperature overnight. The mixture was concentrated and the residue was purified by silica gel column chromatography (petroleum ether: EtOAc =100: ito 1: 1) to give tert-butyl 3-(2- bromoethyl)azetidine-1-carboxylate (5.5 g, 69.4percent yield) as a colorless oil. LC-MS m/z: 208[M+H-56j.
Reference: [1] Patent: WO2017/27684, 2017, A1, . Location in patent: Paragraph 00255
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