1H-Imidazole-1-carboxylic acid, 1,1-dimethylethyl ester

White powder

General procedure: Amine (1 mmol) was added to a magnetically stirred solution of guanidine hydrochloride (15 molpercent) and di-tert-butyl dicarbonate (1.2 mmol) in EtOH (1 mL), at 35-40°C and stirred for appropriate time (Table 1). After completion of the reaction (followed by TLC or GC), EtOH was evaporated under vacuum and the residue either was washed with water to remove the catalyst or was dissolved in CHGeneral procedure: To a mixture of amine (1.0 mmol) and (Boc)General procedure: Fe(OTf)3 (1 molpercent) was added to a magnetically stirred mixture of anamine (1 mmol) and Boc2O (1 mmol) at room temperature. The mixturewas stirred until completion of the reaction (TLC), then diluted withEtOAc and washed with water. The organic layer was dried overanhydrous MgSO4, then the solvent was distillated off under vacuum toyield the highly pure N‑Boc derivativesUnder nitrogen, imidazole was dissolved in anhydrous tetrahydrofuran (THF), and an appropriate amount of di-tert-butyl dicarbonate was dropped slowly into the solution; then reaction was carried out for about 2 hours accompanied by effervescent and exothermic phenomena. After the reaction was completed, the solvent and tert-butyl alcohol byproduct were removed by vacuum reduced pressure concentration to provide compound 2 as white solid, with yield of about 95percent.Under nitrogen system imidazole dissolved in anhydrous tetrahydrofuran (tetrahydrofuran, hereinafter THF) and slowly added dropwise to the appropriate third-butyl dicarbonate (di-tert-butyl dicarbonate), then the reaction exotherm and bubbling, about two hours i.e. the reaction is completed; after completion of the reaction, concentration under reduced pressure, and the solvent was evacuated in vacuo and the third by-product alcohol is removed, to give a white solid of compound 2, producing approximately 95percent.General procedure: AmberlystGeneral procedure: Amine (1 mmol) was added to the mixture of (Boc)General procedure: Boc2O (1.0 mmol) was added to a mixture of phenol or amine (1.0 mmol) andMgBr2 · OEt2 (0.1 mmol) in a round-bottom flask, at which point an evolution of gas occurs, and the reaction mixture was stirred magnetically at room temperature (ifnecessary, reactions was heated to∼60 °C). After complete consumption of the phenolor amine (by thin-layer chromatography, TLC; 3–16 h), the reaction mixture wasdiluted with water and extracted with EtOAc (3 × 20mL), and the combined EtOAcextracts were dried with Na2SO4 and concentrated under vacuum rotary evaporation.The residue was isolated by column chromatography through a bed of silicagel and eluted with 5–30percent ethyl acetate in hexane to afford the desired Bocprotectedproduct.For the N-boc protection of amines, to solution of diboc (1 mmol) in ethanol (5 ml) was added {K*18-crown-6]Br3}n (0.001 mmol). The solution was stirred at room temperature for 1 min. The amine (1 mmol) was then added and solution as stirred at room temperature for an appropriate time (table 1). After completion of the reaction, the solvent was removed by water bath distillation. To the residue was added ethyl acetate (5 ml) and the mixture was filtered (the catalyst is insoluble in n-hexane and ethyl acetate). The solid was washed with ethyl acetate ()10 ml*2) amd combined filtrates were reduced to dryness to yield the pure products.Synthesis of fert-Butyl (3-(methylamino)propyl)carbamate. A mixture of potassium hydroxide powder (20 mol%, 168 mg, 3 mmol), di(lH-imidazol-l-yl)methanone (2.43 g, 15 mmol, ), and tert-butyl alcohol (15 mmol, 1.112 g) in dry toluene (76 mL) was heated at 60 C (oil bath) with stirring for 3 hours under argon atmosphere. Then N- methyl-l, 3-diaminopropane (15 mmol, 1.322 g, 1.566 mL) was added dropwise. The resulting mixture was heated at 60 C for another 3 hours. After allowing the reaction mixture to cool to room temperature, water was added to the mixture. Two layers were separated and the organic layer was washed with brine, dried over sodium sulfate and concentrated to dryness, affording slightly yellow oil (0.966 g). The aqueous phase was extracted with dichloromethane (3 chi 30 mL). The combined organic extracts were dried over sodium sulfate, filtered, and concentrated to afford slightly yellow oil (0.941 g). The two fractions were combined to afford 1.9 g of desired product (10 mmol, 67%). The product was used in the next synthetic step without further purification.

Molecular Weight:168.19
XLogP3:1
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:2
Exact Mass:168.089877630
Monoisotopic Mass:168.089877630
Topological Polar Surface Area:44.1
Heavy Atom Count:12
Complexity:174
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes