123660-45-7

Upstream product

• 501-53-1 benzyl chloroformate 
• 215657-34-4 N-benzyloxycarbonyl-N-(2-fluorophenyl)methanesulfonamide 
• 618-36-0 rac-methylbenzylamine 
• 300561-17-5 N-benzyloxycarbonyl-N-(2,3,4,5,6-pentafluorophenyl)methanesulfonamide 
• 621-84-1 O-benzyl carbamate 
• 98-85-1 1-Phenylethanol 
• 32366-25-9 1-azidoethylbenzene 
• 889673-98-7 C₁₆H₁₅NO₂ 
• 100-41-4 ethylbenzene 
• 13139-17-8 N-(Benzyloxycarbonyloxy)succinimide 
• 75315-63-8 N-(benzyloxycarbonyl)succinimide 
• 1445-91-6 (S)-1-phenylethanol 
• 1035813-57-0 C₁₁H₁₈NP 
• 511244-40-9 N-benzyloxycarbonyl-5,7-dinitroindoline 

Downstream Products

• 909906-72-5 (E)-benzyl 1-phenylethylidenecarbamate 

Relevant academic research and scientific papers

Photochemical protection of amines with Cbz and Fmoc groups

The photochemical conversion of amines into carbamates was achieved using N-Cbz-, N-Fmoc-, and N-Boc-5,7-dinitroindolines. This reaction allows the protection of amines in neutral medium. Primary and unhindered secondary amines were protected to yield their benzyloxycarbonyl- and 9-fluorenylmethoxycarbonyl derivatives efficiently, whereas bulky amines or anilines gave low yields or no product. On the other hand, the formation of N-Boc compounds, although possible, proceeded only with low yields.

Molybdenum(V) chloride-catalyzed amidation of secondary benzyl alcohols with sulfonamides and carbamates

A general and selective method for the direct amidation of secondary benzyl alcohols with both sulfonamides and carbamates is described. This method has been applied to a variety of substrates and the reaction proceeded smoothly at room temperature in the

A practical procedure for the preparation of carbamates from azides

A practical procedure for the direct conversion of azides to carbamates has been found. High yields are obtained when primary and secondary aliphatic azides, as well as α-azido esters, are treated in THF with Me3P and several chloroformates (ClCOOBn, ClCOOMe, ClCOOEt, ClCOOCH2CCl3, ClCOOCH2CH=CH2).

Copper-catalyzed oxidative benzylic C(sp3)-H amination: Direct synthesis of benzylic carbamates

A new efficient strategy to access benzylic carbamates through C-H activation is reported. The use of a catalytic amount of a Cu(i)/diimine ligand in combination with NFSI ((PhSO2)2NF) or F-TEDA-PF6 as oxidants and H2NCO2R as an amine source directly leads to the C-N bond formation at the benzylic position. The mild reaction conditions and the broad substrate scope make this transformation a useful method for the late-stage incorporation of a ubiquitous carbamate fragment onto hydrocarbons. This journal is

A Simple, efficient, Catalyst-Free and Solvent-Less Microwave-Assisted process for N-Cbz Protection of Several amines

A simple, green and chemo-selective method for the N-benzyloxycarbonylation of amines, β-amino alcohols, α-amino esters and sulfonamides has been developed under microwave irradiation. Good to excellent yields of the N-benzyloxy-carbamates compounds were obtained in short times without any side products.

N-Urethane protection of amines and amino acids in an ionic liquid

An efficient, solvent-free protocol for the N-fluorenylmethoxycarbonylation and N-benzyloxycarbonylation of amines is described. The reaction of aliphatic and aromatic amines with FmocOSu and Cbz-Osu in [Bmim][BF4] at room temperature afforded the corresponding N-urethane derivatives in excellent yields and do not require any further purification. The method has been extended to the N-Fmoc and N-Cbz protection of amino acids. Absence of bases, very short reaction times, high yields, selectivity and ease of product separation are some advantages of this protocol.

Rapid assessment of protecting-group stability by using a robustness screen

An experimentally simple method has been developed to rapidly establish the stability of widely utilized silyl, acetal, and carbamate protecting groups to a given set of reaction conditions. Assessment of up to twelve protecting groups in a single experiment has been demonstrated. Evaluation of this protocol in two unrelated synthetic transformations suggests that this method can be used to select appropriate protecting groups in the design of synthetic routes.

Synthesis, X-ray crystallography, and reactions of N-acyl and N-carbamoyl succinimides

A collection of N-acyl and N-carbamoyl succinimides were prepared by acylation of succinimide with acyl chlorides or by ethylene dichloride (EDC) coupling of carboxylic acids. The x-ray crystal structures of N-benzoyl and N-p-nitrobenzoyl succinimides were determined. The N-acyl succinimides were effective in acylating primary amines, a secondary amine, and an aromatic amine. Copyright

Aluminum triflate as a powerful catalyst for direct amination of alcohols, including electron-withdrawing group-substituted benzhydrols

Direct aminations of allylic alcohols, benzylic alcohols, and benzhydrols with electron-withdrawing (F, Br, I, NO2, or CN) substituents were efficiently catalyzed by aluminum triflate [Al(OTf)3] to afford the corresponding biarylamines in high yield, and the dibromo-substituted product was further transformed into letrozole. Copyright

A facile protocol for N-Cbz protection of amines in PEG-600

An efficient and eco-friendly protocol for the chemoselective N-benzyloxycarbonylation of amines was described. The reaction of amines with benzyl chloroformate (Cbz-Cl) in the presence of PEG-600 at room temperature afforded the corresponding N-Cbz derivatives in excellent yields. The method is applicable to the N-Cbz protection of aliphatic (acyclic and cyclic) and aromatic amines.