134746-23-9

Basic information

• Product Name: ethyl 2-(((benzyloxy)carbonyl)amino)-2-chloroacetate
• Synonyms: ethyl 2-(((benzyloxy)carbonyl)amino)-2-chloroacetate
• CAS NO: 134746-23-9
• Molecular Weight: 271.7
• Mol File: 134746-23-9.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: ethyl 2-(((benzyloxy)carbonyl)amino)-2-chloroacetate(CAS DataBase Reference)
• NIST Chemistry Reference: ethyl 2-(((benzyloxy)carbonyl)amino)-2-chloroacetate(134746-23-9)
• EPA Substance Registry System: ethyl 2-(((benzyloxy)carbonyl)amino)-2-chloroacetate(134746-23-9)

Safety Data

• Hazardous Substances Data: 134746-23-9(Hazardous Substances Data)

Upstream product

• 621-84-1 O-benzyl carbamate 
• 64805-08-9 ethyl glyoxylate hydrate 
• 104473-51-0 ethyl 2-(((benzyloxy)carbonyl)amino)-2-hydroxyacetate 
• 924-44-7 glyoxylic acid ethyl ester 

Downstream Products

• 1562347-70-9 ethyl N-benzyloxycarbonyl-α-(4-methoxyphenyl)glycinate 
• 1562347-72-1 ethyl N-benzyloxycarbonyl-α-(5-bromo-2,4-dimethoxyphenyl)glycinate 
• 1562347-74-3 C₂₁H₂₅NO₆ 
• 1562347-77-6 ethyl N-benzyloxycarbonyl-α-(4-(dimethylamino)benzo[1,3]dioxol-5-yl)glycinate 
• 1562347-79-8 ethyl N-benzyloxycarbonyl-α-(N-metylpyrrol-2-yl)glycinate 
• 1562347-85-6 ethyl N-benzyloxycarbonyl-α-(furan-2-yl)glycinate 
• 1562351-82-9 ethyl N-benzyloxycarbonyl-α-(1-methylindol-3-yl)glycinate 
• 1562347-89-0 ethyl N-benzyloxycarbonyl-α-(1H-indol-3-yl)glycinate 
• 1562347-92-5 ethyl N-benzyloxycarbonyl-2-(anthracen-9-yl)glycinate 
• 1562347-97-0 C₁₂H₁₄⁽²⁾HNO₅ 
• 1562347-65-2 ethyl N-benzyloxycarbonyl-α-(2,4-dimethoxyphenyl)glycinate 
• 475603-50-0 ethyl (S)-2-(((benzyloxy)carbonyl)amino)-6-cyanohexanoate 
• 676268-52-3 (S)-2-(((benzyloxy)carbonyl)amino)-8-oxodecanoic acid 

Relevant articles and documents

Asymmetric Synthesis of Protected Unnatural α-Amino Acids via Enantioconvergent Nickel-Catalyzed Cross-Coupling

Interest in unnatural α-Amino acids has increased rapidly in recent years in areas ranging from protein design to medicinal chemistry to materials science. Consequently, the development of efficient, versatile, and straightforward methods for their enanti

Enantioselective Synthesis of α-Allyl Amino Esters via Hydrogen-Bond-Donor Catalysis

We report a chiral-squaramide-catalyzed enantio- and diastereoselective synthesis of α-allyl amino esters. The optimized protocol provides access to N-carbamoyl-protected amino esters via nucleophilic allylation of readily accessible α-chloro glycinates. A variety of useful α-allyl amino esters were prepared, including crotylated products bearing vicinal stereocenters that are inaccessible through enolate alkylation, with high enantioselectivity (up to 97% ee) and diastereoselectivity (>10:1). The reactions display first-order kinetic dependence on both the α-chloro glycinate and the nucleophile, consistent with rate-limiting C-C bond formation. Computational analysis of the uncatalyzed reaction predicts an energetically inaccessible iminium intermediate, and a lower energy concerted SN2 mechanism.

Autocatalytic one pot orchestration for the synthesis of α-arylated, α-amino esters

A novel acetyl chloride-mediated cascade transformation involving three components (benzyl carbamate, ethyl glyoxylate and arene nucleophiles) is reported. Aryl orthogonally protected α-amino acids are obtained in a one pot cascade, using a mild AcOH-AcCl system, via a critical autocatalytic dehydration-activation step ensuring an original and efficient Friedel-Crafts orchestration. The Royal Society of Chemistry 2014.