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Chemistry
Heterocyclic Building Blocks
Isoxazoles
tert-Butyl (5-(tert-butyl)isoxazol-3-yl)carbamate
Chemistry
Heterocyclic Building Blocks
Organic Building Blocks
Isoxazoles
Amines Amides

[ CAS No. 89661-71-2 ] {[proInfo.proName]}

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Chemical Structure| 89661-71-2
Chemical Structure| 89661-71-2
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Product Details of [ 89661-71-2 ]

CAS No. :89661-71-2 MDL No. :MFCD11040522
Formula : C12H20N2O3 Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 240.30 Pubchem ID :-
Synonyms :

Safety of [ 89661-71-2 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 89661-71-2 ]

* 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 [ 89661-71-2 ]

[ 89661-71-2 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 55809-36-4 ]
  • [ 24424-99-5 ]
  • [ 89661-71-2 ]
YieldReaction ConditionsOperation in experiment
54% Procedure for Synthesis of tert butyl N-(5-tert-butyl-isoxazole-3yl)carbamate (Step 1) To a solution of 5-tert-butylisoxazol-3-amine (3.0 g, 21.4 mmol) in tetrahydrofuran (30 ml), lithium bis(trimethylsilyl)amide (1 M in THF, 27 ml, 27 mmol) was added and stirred at room temperature for 40 min. To this reaction mixture, solution of ditertiary butyl dicarbonate (5.1 g, 23 mmol) in tetrahydrofuran (20 ml) was added slowly and stirred at room temperature for 3 h. The reaction mixture was quenched with water (40 ml) and extracted with ethyl acetate (150 ml*3). Combined organic layer was dried over sodium sulfate, and concentrated under vacuum. Crude mass obtained was dissolved in methanol (60 ml), 4 N sodium hydroxide solution (60 ml) was added and stirred at room temperature for 2 h. This reaction mixture was then extracted with ethyl acetate (150 ml*3), washed with water, dried over sodium sulfate and concentrated under vacuum. This crude mass was then purified by silica gel column chromatography to give the desired compound (2.77 g, 54% yield). 1H NMR (CDCl3): 7.25 (bs, 1H), 6.47 (s, 1H), 1.51 (s, 9H), 1.32 (s, 9H),
With dmap; triethylamine; In dichloromethane; 1 , 1 -Dimethylethyl Gamma5-(1 , 1 -dimethylethyl)-3-isoxazolyllcarbannate5-(1 ,1-Dimethylethyl)-3-isoxazolamine (500 mg, 3.57 mmol), Boc20 (0.828 mL, 3.57 mmol), DMAP (4.36 mg, 0.036 mmol) and TEA (0.497 mL, 3.57 mmol) were dissolved in DCM (8 mL) in a 50 mL round bottom flask. The mixture was stirred over night. The mixture was evaporated, and crude 1 ,1-dimethylethyl [5-(1 , 1-dimethylethyl)-3-isoxazolyl]carbamate used without purification. MS (m/z) 241.2 (M+H+).
With dmap; In dichloromethane; at 20℃; for 0.5h; A mixture of <strong>[55809-36-4]3-amino-5-tert-butylisoxazole</strong> (2.00 g, 14.27 mmol), DMAP (0.174 g, 1.427 mmol) and di-tert-butyl dicarbonate (3.64 ml, 15.69 mmol) in DCM (20 ml) was stirred at room temperature for 30 min. The reaction mixture was concentrated and purified by BIOTAGE (40M, 0-20% ethyl acetate) to give the title compound
Reference： [1]Patent: US2016/66574,2016,A1 .Location in patent: Paragraph 0271; 0272; 0273
[2]Patent: WO2013/12500,2013,A1 .Location in patent: Page/Page column 71
[3]Patent: US2018/9796,2018,A1 .Location in patent: Paragraph 0449; 0450

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