Alternatived Products of [ 95729-87-6 ]
Product Details of [ 95729-87-6 ]
CAS No. : | 95729-87-6 |
MDL No. : | MFCD12546654 |
Formula : |
C11H11NO3
|
Boiling Point : |
- |
Linear Structure Formula : | - |
InChI Key : | - |
M.W : |
205.21
|
Pubchem ID : | - |
Synonyms : |
|
Application In Synthesis of [ 95729-87-6 ]
* 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 [ 95729-87-6 ]
- Downstream synthetic route of [ 95729-87-6 ]
- 1
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[ 95729-87-6 ]
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[ 209329-11-3 ]
- 2
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[ 95729-87-6 ]
-
[ 98019-65-9 ]
Yield | Reaction Conditions | Operation in experiment |
|
In methanol; palladium-carbon; |
REFERENCE EXAMPLE 14 STR56 In 250 ml of methanol was dissolved 5 g of compound (43) and the compound was catalytically reduced in the presence of 500 mg of palladium-carbon at normal temperature and normal pressure in a hdyrogen atmosphere. After filtering off the catalyst, methanol was distilled off under reduced pressure. The residue thus formed was crystallized from ether and the crystals thus formed were collected by filtration to provide 2.5 g of the desired product, (R)-2-azetidinone-4-carboxylic acid (44) as the colorless crystals. M. p. 97-101 C. NMR (DMSO-d6, CD3 OD) deltappm: 4.60 (1H, d,d, 4-position hydrogen), 3.23 (1H, d,d, 3-position hydrogen), 2.85 (1H, d,d, 3-position hydrogen) IR (KBr) cm-1: 3310, 1735 (broad), 860 |
- 3
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[ 24424-99-5 ]
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[ 95729-87-6 ]
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[ 161511-90-6 ]
Yield | Reaction Conditions | Operation in experiment |
|
With sodium hydroxide; LiAlH4 In tetrahydrofuran; water |
1.b.c Step 1c.
Step 1c. (R)-1-(t -butyloxycarbonyl)-2-azetidinemethanol A dry round bottom flask was charged with 410 mg (2 mmol) of (R)-benzyl azetidin-2-one-4-carboxylate and 10 mL of dry tetrahydrofuran, then swept with nitrogen and cooled to 0° C. To this clear homogeneous solution was added 10 mL of 1 M LiAlH4 in THF dropwise via syringe. After 76 hours, the reaction was cooled to 0° C. and 400 μL of distilled water was added slowly (vigorous gas evolution). The mixture was stirred for 15 minutes and then 400 μL of 15% NaOH was added and the mixture was stirred an additional 15 minutes. Finally, 800 μL of distilled water was added, the white heterogeneous reaction was allowed to warm to room temperature, and then filtered through a 1/2 inch plug of Celite and concentrated in vacuo to give 420 mg of a light yellow oil. A portion of this oil (310 mg) was treated with 4 mL CH2 Cl2 followed by 460 mg di-tert-butyldicarbonate (2.1 mmol). This cloudy, light yellow mixture was stirred at room temperature for 4.5 hours and then concentrated in vacuo to yield 632 mg of a yellow oil. Flash chromatography (silica gel with 2:1 to 1:1 hexane:ethyl acetate) produced 167 mg of the title compound (61% yield): [α]D20 +22.3 (c 1.28, CHCl3); MS (CI/NH3) m/z: 188 (M+H)+. 1 H NMR (CDCl3, 300 MHz) δ 1.45 (s, 9H), 1.94 (m, 1 H), 2.15 (m, 1 H), 3.68-3.92 (m, 5H), 4.44 (m, 1 H). |