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Chemical Structure| 889952-83-4 Chemical Structure| 889952-83-4
Chemical Structure| 889952-83-4

1-Boc-(3-carboxymethoxy)azetidine

CAS No.: 889952-83-4

4.5 *For Research Use Only !

Cat. No.: A209170 Purity: 98%

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Product Details of [ 889952-83-4 ]

CAS No. :889952-83-4
Formula : C10H17NO5
M.W : 231.25
SMILES Code : O=C(COC1CN(C(OC(C)(C)C)=O)C1)O
MDL No. :MFCD02179034
InChI Key :ASFSRFQPUZSIQT-UHFFFAOYSA-N
Pubchem ID :40429408

Safety of [ 889952-83-4 ]

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

Application In Synthesis of [ 889952-83-4 ]

* 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.

  • Downstream synthetic route of [ 889952-83-4 ]

[ 889952-83-4 ] Synthesis Path-Downstream   1~10

  • 1
  • [ 305-53-3 ]
  • [ 889952-83-4 ]
YieldReaction ConditionsOperation in experiment
Preparation 17; S-Carboxymethoxyazetidine-l-carboxylic acid tert-butyl ester; Anhydrous DMF (5 mL) was added slowly to a stirred mixture of 3-hydroxyazetidine-l- carboxylic acid tert-butyl ester (350 mg, 2.0 mmol) and NaH (121 mg of a 60% dispersion in mineral oil, 3.0 mmol) at 00C. After 15 min, ICH2CO2Na (630 mg, 3.0 mmol) was added, then stirring was continued at 200C for 65 h. The solvent was removed in vacuo, then the residue was partitioned between H2O (15 mL) and EtOAc (10 mL). The organic phase was extracted with saturated aqueous Na2CO3 (2 x 10 mL), then the combined aqueous extracts were acidified to pH 2 with 2 M HCl, before being extracted with EtOAc (2 x 50 mL). The EtOAc extracts were washed with brine, before being dried (MgSO4). Filtration, solvent evaporation, and column chromatography (IH-EtOAc, 1:1) furnished the title compound
  • 2
  • [ 889952-83-4 ]
  • (2S,5R)-6-(benzyloxy)-7-oxo-1,6-diazabicyclo[3.2.1]ctane-2-carbohydrazide [ No CAS ]
  • C24H33N5O7 [ No CAS ]
YieldReaction ConditionsOperation in experiment
45% With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In N,N-dimethyl-formamide; at 20℃; Example 43: Synthesis of(2S,5R)-2-(5-((azetidin-3-yloxy)methyl)-l,3,4-oxadiazol-2-yl)-7- oxo-l,6-diaz.abicyclo[3.2.1 loctan-6-yl hydrogen sulfate (Compound 744) ESI-MS (EI+, m/z): 376.2. 'H NMR (300 MHz, D20) delta 4.78 (s, 2H), 4.74 (d, / = 6.4 Hz, 1 H), 4.66 - 4.56 (m, 1H), 4.34 - 4.22 (m, 2H), 4.16 (br s, 1H), 4.06 - 3.91 (m, 2H), 3.23 - 3.04 (m, 1H), 2.88 (d, / = 12.3 Hz, 1H), 2.35 - 2.00 (m, 3H), 2.00 - 1.80 (m, 1H).
  • 3
  • [ 141699-55-0 ]
  • [ 889952-83-4 ]
  • 4
  • tert-butyl 3-(2-(benzyloxy)-2-oxoethoxy)azetidine-1-carboxylate [ No CAS ]
  • [ 889952-83-4 ]
YieldReaction ConditionsOperation in experiment
86% With hydrogen; palladium; In methanol; at 20℃; Example 43: Synthesis of(2S,5R)-2-(5-((azetidin-3-yloxy)methyl)-l,3,4-oxadiazol-2-yl)-7- oxo-l,6-diaz.abicyclo[3.2.1 loctan-6-yl hydrogen sulfate (Compound 744) ESI-MS (EI+, m/z): 376.2. 'H NMR (300 MHz, D20) delta 4.78 (s, 2H), 4.74 (d, / = 6.4 Hz, 1 H), 4.66 - 4.56 (m, 1H), 4.34 - 4.22 (m, 2H), 4.16 (br s, 1H), 4.06 - 3.91 (m, 2H), 3.23 - 3.04 (m, 1H), 2.88 (d, / = 12.3 Hz, 1H), 2.35 - 2.00 (m, 3H), 2.00 - 1.80 (m, 1H).
  • 5
  • [ 889952-83-4 ]
  • C24H31N5O6 [ No CAS ]
  • 6
  • [ 889952-83-4 ]
  • C17H25N5O6 [ No CAS ]
  • 7
  • tert-butyl 3-(2-methoxy-2-oxoethoxy)azetidine-1-carboxylate [ No CAS ]
  • [ 889952-83-4 ]
YieldReaction ConditionsOperation in experiment
57.7% With water; lithium hydroxide; In tetrahydrofuran; at 20℃; To a solution of tert-butyl 3-(2-methoxy-2-oxoethoxy)azetidine-i-carboxylate (1.1 g, 4.50 mmol) in THF (10 mL) was added LiOH (216 mg, 9.0 mmol) and water (5mL).The resulting mixture was stirred at room temperature overnight and THF was removed under vacuum. The aqueous residue was acidified to pH 4 by additionofHCl (1 M) and extracted with EtOAc (50 mL x 2). The organic layers were dried over anhydrous Na2SO4 and concentrated to give 2-(( 1 -(tert-butoxycarbonyl)azetidin-3 -yl)oxy)acetic acid (600 mg, 57.7% yield) as a colorless oil, which was directly used to the next reaction without purification. LC15 MS m/z: 231 [M+Hf?.
  • 8
  • [ 889952-83-4 ]
  • 2-(azetidin-3-yloxy)-N-methylacetamide trifluoroacetate [ No CAS ]
  • 9
  • [ 889952-83-4 ]
  • [ 593-51-1 ]
  • tert-butyl 3-(2-(methylamino)-2-oxoethoxy)azetidine-1-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
59.9% Toa solution of 2-((i-(tert-butoxycarbonyl)azetidin-3-yl)oxy)acetic acid (600 mg, 2.60 mmol) in DCM (10 mL) was added HOBt (526.5 mg, 3.90 mmol) followed by addition of EDCI (747.2 mg, 3.90 mmol) in portions at 0C. DIPEA (1.34 g, 10.4 mmol) wasadded dropwise. The resulting mixture was stirred at 0C for 30 mm, and methylamine hydrochloride (351.4 mg, 5.20 mmol) was added at 0C. The reaction was then stirred at room temperature overnight. The mixture was then diluted with water and extracted with DCM. The organic layers were washed with brine, dried over Na2504, filtered and concentrated. The residue was purified by silica gel column chromatography (petroleum ether: EtOAc = 100: 11: 1) to give tert-butyl 3-(2-(methylamino)-2-oxoethoxy)azetidine-i-carboxylate (380 mg,5 9.9%) as a colorless oil. LC-MS m/z: 245 [M+Hf?.
  • 10
  • [ 889952-83-4 ]
  • [ 76-05-1 ]
  • 2-(azetidin-3-yloxy)acetic acid trifluoroacetic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
In dichloromethane; at 20℃; for 2h; To a solution of <strong>[889952-83-4]2-((1-(tert-butoxycarbonyl)azetidin-3-yl)oxy)acetic acid</strong> (500 mg, 2.16 mmol) in DCM (5 mL) was added TFA (2 mL). The mixture was stirred at r.t. for 2hr. The reaction mixture was concentrated and the residue was used in the next step without further purification.
 

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