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CAS No. : | 248921-66-6 | MDL No. : | MFCD09751020 |
Formula : | C12H23NO5 | Boiling Point : | No data available |
Linear Structure Formula : | - | InChI Key : | BPYLRGKEIUPMRJ-MRVPVSSYSA-N |
M.W : | 261.31 | Pubchem ID : | 6992546 |
Synonyms : |
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Signal Word: | Warning | Class: | |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | |
Hazard Statements: | H302-H315-H319-H335 | Packing Group: | |
GHS Pictogram: |
* 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.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
480 mg (100%) | With triethylamine; In dichloromethane; ethyl acetate; | Step A: 2(R)-t-Butoxycarbonylamino-3-(t-butoxy)-N-[2,3,4,5-tetrahydro-2-oxo-1H-1-benzazepin-3(R)-yl]propanamide To a solution of 200 mg (1.13 mmol) of 3(R)-amino-2,3,4,5-tetrahydro-1H-1-benzazepin-2-one (Example 1, Step B) in 8 mL of dry methylene chloride was added 0.206 mL (1.48 mmol) of triethylamine, 553 mg (1.25 mmol) of <strong>[248921-66-6]BOC-D-serine t-butyl ether</strong> followed by 602 mg (1.36 mmol) of benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate. The reaction mixture was stirred at room temperature for 2 hours then diluted with 100 mL of ethyl acetate, washed with 25 mL of 5% aqueous citric acid, 25 mL of saturated sodium bicarbonate and 25 mL of brine. The organic layer was dried over magnesium sulfate, filtered and the solvents removed under vacuum. The residue was purified by flash chromatography on silica gel, eluding with ethyl acetate/hexane (55:45) to afford 480 mg (100%) of the product as a white foam. 1 H NMR (200 MHz,CDCl3): 1.20 (s,9H), 1.47 (s,9H), 1.92 (m,1H), 2.55-3.02 (m,3H), 3.38 (t,8 Hz,1H), 3.78 (m,1H), 4.15 (m,1H), 4.52 (m,1H), 5.45 (s,1H), 7.00 (m,1H), 7.10-7.35 (m,3H), 7.68 (d,4 Hz,1H), 8.05 (s,1H). FAB-MS: calculated for C22 H33 N3 O5 419; found 420 (M+H,20%), 426 (M+Li,40%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; In dichloromethane; at 0 - 20℃; | STEP A: (l-fe/t-Butoxymethyl-2-morpholin-4-yl-2-oxo-ethyl)-(J?)-carbamic acid fert-butyl ester To an ice cooled solution of morpholine (0.6 mL, 6.9 mmol) , <strong>[248921-66-6]Boc-D-Ser(tBu)-OH</strong> (3 g, 6.8 mmol) and HOBT (1.2 g, 9 mmol) in CH2Cl2 (50 mL), TEA (1.9 mL) was added followed by addition of 1,3-dimethylamino propyl-3-ethylcarbodiimide (EDC, 1.7 g, 8.6 mmol). The reaction mixture was allowed to warm to room temperature and was then stirred overnight. EtOAc (200 mL) was added to the reaction mixture. This resulting solution was washed with dilute HCl solution, NaHCO3 (aq.) solution, and NaCl (aq.) solution. The organic <n="109"/>layer was dried over MgSO4, filtered, and evaporated to yield (l-tert-butoxymethyl-2- morpholin-4-yl-2-oxo-ethyl)-(/?J-carbamic acid tert-butyl ester as a crude oil. MH+ 331.2 |
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