* 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.
With potassium hydroxide; In ethanol; water; toluene;
The starting material can be manufactured, for example, as follows: 50 ml of ethanol, 50 g of potassium hydroxide and 8.8 ml of water are added to 39.8 g of 1-ethoxycarbonyl-4-[2-(3-chlorophenyl)-ethyl]-piperazine, obtainable by reacting 17.7 g of 1-ethoxycarbonylpiperazine and 24.6 g of 2-(3-chlorophenyl)-ethyl bromide while heating at 120-125 under nitrogen, and the whole is heated under reflux for 3 hours. The whole is then allowed to cool, is diluted with 300 ml of water and 300 ml of toluene and shaken thoroughly, and then the organic phase is separated off, washed with saturated sodium chloride solution, dried over sodium sulphate and concentrated to dryness by evaporation under reduced pressure. 1-[2-(3-chlorophenyl)-ethyl]piperazine is obtained and can be purified via the hydrochloride (m.p. 260) from which it can then be freed again by treatment with sodium hydroxide solution, separation with diethyl ether and evaporation of the latter.
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In dichloromethane; at 20℃; for 16h;
Example 133: 4-((S)-2-[5-(3,3-Dimethyl-2-oxo-butoxy)-1 -phenyl-1 H-pyrazole-3-carbonyl]- aminoJ-S-methoxycarbonylamino-propionyO-piperazine-i-carboxylic acid ethyl ester; (i) 4-((S)-2-Benzyloxycarbonylamino-3-tert-butoxycarbonylamino-propionyl)- piperazine-1-carboxylic acid ethyl ester; To a solution of 5 g of (S)-2-Benzyloxycarbonylamino-3-tert-butoxycarbonylamino- propionic acid, 3 g of triethylamine, 2.2 g of HOBT and 2.8 g of EDC in 50 ml of DCM, 2.3 g of Piperazine-1-carboxylic acid ethyl ester was added at RT and stirred for 16 h. The reaction mixture was then diluted with water and then extracted with 300 ml of DCM. The organic phase was washed with diluted saturated aqueous sodium hydrogen carbonate solution and dried over MgSO4. The solvents were removed under reduced pressure. The crude product was subjected to the next reaction step without further purification. Yield: 10.7 g.
With N-ethylmorpholine;; O-<[cyano(ethoxycarbonyl)methylene]amino>-1,1,3,3-tetramethyluronium tetrafluoroborate; In N,N-dimethyl-formamide; at 0℃; for 1h;
Example 92: 4-[(S)-4-Acetylamino-2-({5-[2-((S)-2-cyclobutylcarbamoyl-pyrrolidin-1- yl)-2-oxo-ethoxy]-1 -phenyl-1 H-pyrazole-3-carbonyl}-amino)-butyryl]-piperazine-1 - carboxylic acid ethyl ester; i) 4-[(S)-4-tert-Butoxycarbonylamino-2-(9H-fluoren-9-ylmethoxycarbonylamino)- butyryl]-piperazine-1 -carboxylic acid ethyl ester; To a solution of 1.33 ml 1-ethoxycarbonylpiperazine, 1.27 ml N-ethylmorpholine and 4.0 g N-alpha-Fmoc-N-beta-Boc-L-diaminobutyric acid in 40 ml DMF were added 2.98 g TOTU at 0 0C. After 1 h the reaction mixture was diluted with 100 ml ethyl acetate and subsequently extracted with aqueous LiCI (4 percent), half-saturated aqueous NaHCO3 and water. The crude <n="118"/>product obtained after evaporation of the solvent was used in the subsequent reaction. Yield: 4.96 g colorless foam.
(3R,3aR,5S,8aR,9aR)-5,8a-dimethyl-3-[4-(ethoxycarbonyl)piperazin-1-yl]methyl}-3a,5,6,7,8,8a,9,9a-octahydronaphtho[2,3-b]furan-2(3H)-one[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
77%
In methanol; at 20℃; for 12h;
General procedure: Lactone (1 mmol) in MeOH (5 mL) wasstirred, treated with a solution of piperazine (1 mmol) in MeOH (2 mL), and left at room temperature. The course of thereaction was monitored by TLC. If the product did not precipitate, the solvent was evaporated in vacuo after the reaction wascomplete. The residue was recrystallized from a suitable solvent (usually C6H6-hexane mixtures). Compounds 5a-e, 6a-d,and 7a,d,e were prepared by this method.
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