Carbobenzoxy Chloride

CARBOBENZOXY CHLORIDE CARBOFURAN CARBON DIOXIDE CARBON DISULFIDE... 

Chemical Designations - Synor ms Carbobenzoxy Chloride Chloroformic Acid, Benzyl Ester Benzylcarbonyl Chloride Benzyl Chlorocarbonate Chemical Formula C HjCH OCOCl. Ohservahle Characteristics - Physical State (as normally sh ed) Liquid Color. Colorless Odor. Irritating sharp, penetrating. 

Preparation of L-(-)-y-Benzyloxycarbonylamino-a-Hydroxybutyric Acid L-(-)-7-amino-o-hydroxybutyric acid (7.4 g, 0,062 mol) was added to a solution of 5.2 grams (0.13 mol) of sodium hydroxide in 50 ml of water. To the stirred soiution was added dropwise at 0 -5°C over a period of 0.5 hour, 11.7 grams (0.06B mol) of carbobenzoxy chloride and the mixture was stirred for another hour at the same temperature. The reaction mixture was washed with 50 ml of ether, adjusted to pH 2 with dilute hydrochloric acid and extracted with four BO ml portions of ether. The ethereai extracts were combined, washed with a small amount of saturated sodium chloride solution, dried with anhydrous sodium sulfate and filtered. The filtrate was evaporated in vacuo and the resulting residue was crystallized from benzene to give 11.6 grams (74%) of colorless plates MP 78.5° to 79.5°C. 

An important example is the preparation of carbobenzoxy chloride (PhCH20C0Cl) from phosgene and benzyl alcohol. This compound is widely used for protection of amino groups during peptide synthesis (see 10-55). 

CARBOBENZOXY CHLORIDE AND DERIVATIVES (Formic acid, chloro-, benzyl ester)... 

Carbazole, d751 Carbitol, e41a Carbitol acetate, e42 Carbobenzoxy chloride, b91 Carbolic acid, p65... 

Problem 21.18 Write structural formulas for the products of the reactions of (a) alanine + carbobenzoxy chloride (C H,CH,OCOCI) (b) tyrosine + aq. Br, and the product reacted with (CH,),SO< + NaOH. ... 

PhCH,0C=0 1 (Z) PhCH,OCOCl Carbobenzoxy chloride H,/Pi or cold HBr. HOAc PhCH) -t- CO2 + peptide PhCHjBr + CO2 -E peptide... 

N-(Benzyloxycarbonyloxy)succinimide N-hydroxysuccinimide (23 g, 0.2 mole) was dissolved in 200 ml of aqueous NaOH solution (9 g, 0.22 mole). To the stirred solution was added dropwise 34 g (0.2 mole) of carbobenzoxy chloride with water-cooling. The mixture was stirred overnight at room temperature, and the precipitate which separated was collected by filtration, washed with water, and air dried. Yield 41.1 g (82%). Recrystallization from benzene-n-hexane (10 1) gave colorless prisms melting at 78°-79°C. 

SYNS BENZYLCARBONYL CHLORIDE BENZYL CHLOROCARBONATE pOT) BENZYL CHLOROFORMATE pop BENZYLOXYCARBONYL CHLORIDE BZCF CARBOBENZOXY CHLORIDE CARBOBENZYLOXY CHLORIDE CHLOROFORMIC ACID BENZYL ESTER... 

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