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Structure of 1035351-06-4

Chemical Structure| 1035351-06-4

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Product Details of [ 1035351-06-4 ]

CAS No. :1035351-06-4
Formula : C9H15NO5
M.W : 217.22
SMILES Code : O=C(C1(O)CN(C(OC(C)(C)C)=O)C1)O
MDL No. :MFCD24465599
InChI Key :JUVBVTZAIHSJDI-UHFFFAOYSA-N
Pubchem ID :59859689

Safety of [ 1035351-06-4 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Application In Synthesis of [ 1035351-06-4 ]

* 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 [ 1035351-06-4 ]

[ 1035351-06-4 ] Synthesis Path-Upstream   1~5

  • 1
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YieldReaction ConditionsOperation in experiment
43% With potassium carbonate In tetrahydrofuran; water at 0 - 20℃; 50b (6.06 g, 43.0 mmol) was dissolved in tetrahydrofuran / H20 (60 / 60 mL), followed by the addition of potassium carbonate (18.0 g, 129 mmol) at 0 °C and di-tert-butyl dicarbonate (10.3 g, 47.2 mmol. The resulting mixture was stirred overnight at room temperature, then concentrated under reduced pressure. The pH value of the solution was adjusted to between 3 and 4 with aqueous HC1 (3 M). The resulting solution was extracted four times with ethyl acetate and the organic layers combined and dried over anhydrous sodium sulfate and concentrated under reduced pressure. The crude residue was re-crystallized from petroleum ether / ethyl acetate (10 / 1) to give the title compound (4 g, 43percent) as a white solid.
References: [1] Patent: WO2013/96771, 2013, A1, . Location in patent: Page/Page column 146.
[2] Patent: WO2007/44515, 2007, A1, . Location in patent: Page/Page column 214-215.
[3] Patent: WO2008/76415, 2008, A1, . Location in patent: Page/Page column 384-385.
[4] Patent: WO2008/124085, 2008, A2, . Location in patent: Page/Page column 232-233.
  • 2
  • [ 398489-26-4 ]
  • [ 7677-24-9 ]
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YieldReaction ConditionsOperation in experiment
7%
Stage #1: at 20℃; for 18 h; Inert atmosphere
Stage #2: With hydrogenchloride In water; acetic acid for 3 h; Reflux
To a solution of ieri-butyl 3-oxoazetidine-l-carboxylate LII (2.0 g, 11.7 mmol) in THF (50 mL) under an argon atmosphere was added Znl2 (0.11 mg, cat) followed by TMSCN (1.62 g, 16.4 mmol). The mixture was stirred at room temperature for 18 h, and was concentrated to dryness under reduced pressure. The residue was dissolved in EtOAc (100 mL), washed with aqueous NaHC03 and water and then concentrated to dryness. The residue was dissolved in HOAc (25 mL) and treated with concentrated aqueous HCI (25 mL). The mixture was heated at reflux for 3 h and was concentrated to dryness. The residue was dissolved in iPrOH (20 mL) and 2 M aqueous NaOH (20 mL) followed by Boc20 (1.66 g, 8.0 mmol) were added. The iPrOH was removed with a rotary evaporator, water (30 mL) was then added to the residue and the mixture was extracted with Et20 (2 x 30 mL). The aqueous phase was acidified with 1 N aqueous HCI to pH=2 and extracted with EtOAc (3 x 30 mL). The organic phase was dried over Na2S04, filtered and concentrated under reduced pressure. The crude product was purified by column chromatography on silica gel (100percent EtOAc-->l:l EtOAc:MeOH) affording l-(feri-butoxycarbonyl)-3-hydroxyazetidine-3-carboxylic acid LIII (0.17 g, 0.79 mmol, 7percent). ESMS found for C9H15N05 m/z 216 (M-H)".
References: [1] Patent: WO2011/143497, 2011, A1, . Location in patent: Page/Page column 49; 50.
  • 3
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YieldReaction ConditionsOperation in experiment
320 mg With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; [0184] tert-butyl 3-cyano-3-((trimethylsilyl)oxy )azetidine-1-carboxylate (0.79 g, 2.9 mmole) was dissolved in amixture of acetic acid ( 4.4 mL) and concentrated hydrochloricacid (3.4 mL) and heated to 100° C. for 2 hours. Thesolvent was evaporated exhaustively and then co-evaporated(x3) with toluene. The resulting residue was triturated withether/hexane and filtered to give the desired product in crudeform as a yellow semisolid. This material was suspended in10 mL DCM and diisopropylamine (1.1 mL, 6.4 mmole) wasadded followed by di-tert-butyl dicarbonate (956 mg, 4.4mmole) was added and stirred at room temperature overnight.The reaction mixture was diluted with DCM and partitionwith water. The aqueous layer was brought to pH -3 with 1MHCI and then extracted 4 times with DCM. The combinedorganics were dried over sodium sulfate and filtered andevaporated to give 320 mg (50percent) of 1-(tert-butoxycarbonyl)-3-hydroxyazetidine-3-carboxylic acid as a white solid.
References: [1] Patent: WO2011/44503, 2011, A1, . Location in patent: Page/Page column 60; 71.
[2] Patent: US2012/295874, 2012, A1, . Location in patent: Page/Page column 246-247.
[3] Patent: US2016/31892, 2016, A1, . Location in patent: Paragraph 0183-0184.
  • 4
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References: [1] Patent: WO2008/124821, 2008, A1, . Location in patent: Page/Page column 64-65.
  • 5
  • [ 398489-26-4 ]
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References: [1] Patent: WO2008/124821, 2008, A1, .
 

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