1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride

White crystalline powder

EDC (N-ethyl-N’-(3-dimethylaminopropyl)carbodiimide) carbodiimide reagent for the activation of carboxylic acid and their subsequent coupling with amines. EDC is water soluble and provides a reliable method for activating carboxylic acids in aqueous media.

EDC-HCl, or 1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride, is a white crystalline powder that easily deliquescent and can dissolve in both water and ethanol. It is commonly used as an activating reagent in amide synthesis to activate carboxyl groups. It can also activate phosphate groups, cross-link proteins and nucleic acids, and produce immunocouplers. EDC-HCl is commonly applied in the pH range of 4.0-6.0 and is often used in conjunction with N-Hydroxysuccinimide (NHS) or N-Hydroxysulfosuccinimide sodium salt to improve coupling efficiency.

It is an excellent H2O-soluble peptide coupling reagent. It is purified by dissolving (ca 1g) in CH2Cl2 (10mL) at room temperature and then add dry Et2O (~110mL) dropwise and the crystals that separate are collected, washed with dry Et2O, recrystallised from CH2Cl2/Et2O and dried in a vacuum over P2O5. It is important to work in a dry atmosphere or work rapidly and then dry the solid as soon as possible. The material is moderately hygroscopic, but once it becomes wet it reacts slowly with H2O. Store it away from moisture at -20o to slow down the hydrolysis process. The free base has b 47-48o/0.27mm, 53-54o/0.6mm, n 1.4582. The methiodide is recrystallised from CHCl3/EtOAc, the crystals are filtered off, washed with dry Et2O, recrystallised from CHCl3/Et2O, and dried in vacuo over P2O5, m 93-95o, 94-95o. [Sheehan et al. J Am Chem Soc 87 2492 1965, Sheehan & Cruickshank Org Synth Coll Vol V 555 1973.] § A polymer bound version is commercially available.

Weigh 24ml of carbon disulfide dissolved in 150ml methanol, 43.8 g of N, N'-dimethylpropylenediamine was slowly added dropwise to control the temperature at 10-15 ° C, The dropwise addition process was carried out with a white solid which was added dropwise at 20 ° C for 2 hours, filtered and washed with methanol to give 75 g of a white solid (Intermediate 1) in 96percent yield.75 g of the product was weighed, 200 ml of dichloromethane was added, and the temperature was controlled at 10-15 ° C. 45.8 g of triethylamine was added, followed by slowly dropping 50.3 g of ethyl chloroformate, dropping for 2 hours, After the dropwise addition was carried out for 1 hour, the organic phase was washed, washed, filtered and dried to give the product (Intermediate 2).25.2 g of ethylamine (containing 70percent water) was weighed, 180 ml of dichloromethane was added, Cooling to 10-15 ° C, slowly dropping intermediate 2, dropping finish for 1 hour, The organic phase was washed with an alkali of pH 11-12, dried, under reduced pressure, and concentrated to give 90 g of an oil, (Intermediate 3)0.02 g of EDTA was added and oxidized at 30 ° C with 630 g of sodium hypochlorite at a mass concentration of 10percent. After completion of the oxidation, Extraction layer, the organic phase after drying and vacuum concentration 30 , the solvent evaporated, the vacuum distillation to get EDC, Purity 99.4percent;41.4 g of pyridine hydrochloride was weighed, 120 ml of dichloromethane was added, and the mixture was heated at 30 ° C, Slowly dropping the distillation of the EDC, first dissolved, and then precipitation of crystals, dripping finished, cooling to 5 , Crystallization 1h, filtration, to be 71.2g EDC hydrochloride, purity 99.5percentYield 81percent (based on N, N'-dimethylpropylenediamine).

Protein and nucleic acid cross-linking reagent, water-soluble carbodiimide type condensing agent that can realize rapid peptide condensation reaction. The molecule of EDC (or EDAC) has a linear structure and is used in the condensation reaction of carboxyl group and primary amine, and has been widely used. Used as a peptide condensing agent and cross-linking agent. This product is a water-soluble carbodiimide. It is mainly used as a dehydrating agent in the synthesis of peptides, proteins and nucleotides. It can realize rapid peptide condensation reaction. Condensing agent. Water-soluble concentration reagent; general carbonyl activating reagent, used in the process of amide and secondary amine bonding; can react with phosphate groups; used in peptide synthesis; protein and nucleic acid cross-linking; preparation such as immunological cross-linkers, typical Under conditions, pH 4.0-6.0 and no buffer, under special conditions, the use of amine and carboxylate buffers must be avoided; water-soluble peptide coupling agent; used for carbonyl modification in protein; used for ester synthesis

1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride is used as a carboxyl activating agent. It plays a vital role for immobilization of large biomolecules in association with N-hydroxysuccinimide. It is also used in the acylation of phosphoranes.