21601-78-5

Usage

InChI:InChI=1/C15H12O4/c16-14(17)13(11-7-3-1-4-8-11)15(18)19-12-9-5-2-6-10-12/h1-10,13H,(H,16,17)

Upstream product

• 65-85-0 benzoic acid 
• 1005500-77-5 N,4-dimethyl-N-(phenylethynyl)benzenesulfonamide 
• 2613-89-0 phenylmalonic acid 
• 108-95-2 phenol 

Downstream Products

• 27025-49-6 carfecillin 

Relevant academic research and scientific papers

Synthesis method of carbenicillin drug intermediate phenylmalonate monophenyl ester

A synthesis method of carbenicillin drug intermediate phenylmalonate monophenyl ester comprises steps as follows: (i) 0.17-0.19 mol of phenylmalonic acid and 100 ml of a toluene solution are added to a reaction container provided with a stirrer and a thermometer, 0.18 mol of N-(3-hydroxyphenyl)acetamide is added slowly, the solution temperature is controlled within 80-85 DEG C, the reaction time is controlled within 4-5 h, toluene is evaporated out through reduced pressure distillation, 100 ml of an ethylene diamine solution and 0.16-0.17 mol of phenol are added to a remainder, heating reflux is performed for 3-3.5 h, the solution temperature is decreased to 40-45 DEG C, washing is performed with 50 ml of a salt solution, extraction is performed with a potassium hydroxide solution, the pH of the solution is controlled to range from 8 to 9, extract solutions are mixed and washed with 200 ml of a toluene solution, a water layer is washed with a potassium bicarbonate solution, a produced oily matter is fully extracted with a methylamine solution, a methylamine layer is washed with water and dehydrated with a dehydrating agent, a solvent is evaporated out, produced solids are recrystallized with isopropyl alcohol, and colorless acicular crystals, namely, phenylmalonate monophenyl ester, are obtained.

Catalytic Ynamide Oxidation Strategy for the Preparation of α-Functionalized Amides

A Lewis acid-catalyzed alkyne oxidation strategy has been developed to produce diverse α-functionalized amides from readily and generally available ynamides. An efficient zinc(II)-catalyzed oxidative azidation and thiocyanation has been achieved, providing facile access to synthetically useful α-azido amides and α-thiocyanate amides, respectively. This chemistry can also be extended to oxidative halogenations by employing the 2-halopyridine N-oxide as both the oxidant and the halogen source, and its mechanistic rationale is also supported by density functional theory calculations. Moreover, NaBARF has been demonstrated to catalyze such an alkyne oxidation effectively, thus further excluding the metal carbene pathway in this cascade reaction.

Preparation, hydrolysis, and oral absorption of alpha-carboxy esters of carbenicillin.

Twelve alpha-carboxy esters of carbenicillin, a parenteral broad spectrum semisynthetic penicillin, were synthesized and examined as potential oral carbenicillin derivatives. The rates at which the esters were hydrolyzed in vitro to carbenicillin by animal and human tissues were compared and the carbenicillin serum levels arising after oral administration of the esters were measured in squirrel monkeys and human volunteer subjects. The alpha-carboxyphenyl ester of carbenicillin [carfecillin (British Pharmacopoeia approved name), BRL 3475] WAS SELECTED FOR FURTHER STUDY AND IS PRESENTLY UNDERGOING CLInical trial.