CAS RN: 530-62-1 | Product Number: C0119
1,1'-Carbonyldiimidazole [Coupling Agent for Peptides Synthesis]
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|Purity / Analysis Method||>97.0%(T)|
|Molecular Formula / Molecular Weight||C__7H__6N__4O = 162.15|
|Physical State (20 deg.C)||Solid|
|Store Under Inert Gas||Store under inert gas|
|Condition to Avoid||Moisture Sensitive,Heat Sensitive|
|Reaxys Registry Number||6826|
|PubChem Substance ID||87565300|
|SDBS (AIST Spectral DB)||21181|
|Merck Index (14)||1819|
|Appearance||White to Light yellow powder to crystal|
|Purity(Neutralization titration)||min. 97.0 %|
|Melting point||115.0 to 122.0 °C|
|Melting Point||118 °C|
|Hazard Statements||H302 : Harmful if swallowed.
H314 : Causes severe skin burns and eye damage.
|Precautionary Statements||P260 : Do not breathe dust or mist.
P280 : Wear protective gloves/ protective clothing/ eye protection/ face protection.
P303 + P361 + P353 : IF ON SKIN (or hair): Take off immediately all contaminated clothing. Rinse skin with water.
P301 + P330 + P331 : IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P304 + P340 + P310 : IF INHALED: Remove person to fresh air and keep comfortable for breathing. Immediately call a POISON CENTER/doctor.
P305 + P351 + P338 + P310 : IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Immediately call a POISON CENTER/doctor.
To a solution of N-carbobenzoxyglycine (2.10 g, 10 mmol) in anhydrous tetrahydrofuran (10 mL) was added 1,1'-carbonyldiimidazole (1.64 g, 10 mmol). The mixture was stirred at room temperature for 4 hours. L-tyrosine ethyl ester (2.10 g, 10 mmol) was added to the reaction mixture. The mixture was stirred at room temperature overnight. The solvent was removed under reduced pressure. The residue was dissolved in ethyl acetate (30 mL), treated with 1 mol/L HCl solution (50 mL), and stirred for 10 min. The organic layer was separated and the aqueous layer was extracted with ethyl acetate (20 mL x 2). The combined organic layers were washed with saturated aqueous NaHCO3 solution (30 mL), washed with brine (30 mL), dried over Na2SO4 and filtered. The solvent was removed under reduced pressure. The residue was purified by flash column chromatography (eluent: dichloromethane/ethyl acetate, 90/10→75/25→50/50) to obtain 1 as a white solid (3.54 g, 88%).
The reaction mixture was monitored by TLC (hexane/ethyl acetate = 5/1, Rf = 0.17) and 1H NMR. After the reaction mixture was concentrated and quenched by 1 mol/L HCl solution, the recrystallization with ethanol was conducted. Sticky white solid was precipitated at low temperature but it can't be filtered.
Analytical Data（Compound 1）
1H NMR (400 MHz, CDCl3); δ 7.35 (m, 5H), 6.92 (d, J =8.24 Hz, 2H), 6.67(dd, 3J =8.24 Hz, 4J =1.83 Hz, 2H), 6.45(d, J =6.87 Hz, 1H), 5.69 (s, 1H), 5.40 (br s, 1H), 5.12 (s, 2H), 4.81(q, J =5.95 Hz, 1H), 4.18 (q, J =7.32 Hz, 2H), 3.84 (m, 2H), 3.03 (m, 2H), 1.27 (t, J=7.32 Hz, 4H)
13C NMR (101 MHz, CDCl3); δ 171.55, 168.74, 156.61, 155.24, 135.99, 130.50, 130.39, 128.57, 128.29, 128.14, 126.93, 115.52, 115.37, 67.30, 61.78, 61.50, 53.16, 44.31, 36.95, 14.17, 14.07.
- N,N'-Carbonyldiimidazole, a New Peptide Forming Reagent
To a solution of N-Cbz-glycine (2.09 g, 0.010 mol) in dry THF (10 mL) is added 1,1’-carbonyldiimidazole (CDI) (1.62 g, 0.010 mol). After stirring for 1.5 hour, L-tyrosine ethyl ester (2.09 g, 0.010 mol) is added to the solution and the reaction mixture is stirred overnight. Then THF is removed by an evaporator and 1 N-HCl (50 mL) is added. Cooling of the solution gives a solid. This is washed with water and 5% NaHCO3. The solid is filtered and washed with water again. After drying, the product is recrystallized from 50% ethanol to give ethyl N-Cbz-glycine- L -tyrosine ethyl ester (3.79 g, yield 95%).
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