A -Chloroacetamide

The carboxamidomethyl ester was prepared for use in peptide synthesis. It is formed from the cesium salt of an A-protected amino acid and a-chloroacetamide (60-85% yield). It is cleaved with 0.5 M NaOH or NaHCOa in DMF/H2O. It is stable to the conditions required to remove BOC, Cbz, Fmoc, and r-butyl esters. It cannot be selectively cleaved in the presence of a benzyl ester of aspartic acid. ... 

Condensation, of 2-aminobiphenyl with boron trichloride, 46, 65 of a-chloroacetamide with oxalyl chloride, 46,16... 

The electrophilic ring opening of iV-allyl HHT 53 with chloroacetyl chloride gave N-allyl- -chloromethyl-a-chloroacetamide 54, which was then alkylated with the diethyl ester of a-aminomethylphosphonic acid (AMPA) to generate the imidazolone 55. Subsequent hydrolysis of 55 gave GLYH3 (57). 

Stable to acid and base in the pH range 3-8. Thenylchlor is a chloroacetamide herbicide for the preemergence and post-planting control of annual grass and broad-leaved weeds in paddy rice The residue definition is for the parent, thenylchlor, only... 

Chloriminovanadium trichloride, 4165 A-Chloroacetamide, 0789 A-Chloroallylamine, 1202 A -Chloro-3 -aminopropyne, 1129 A -Chloro-3 -aminopropyne, 1129 1-Chloroaziridine, 0786 1-Chlorobenzotriazole, 2150 A -Chloro-bis(2-chloroethyl)amine, 1590 A-Chlorobis(trilluoromethanesulfonyl)imide, 0596 A-Chlorocinnamaldimine, 3126 A -Chlorodimethylamine, 0895 A -Chloro-4,5-dimethyltriazole, 1490 A -Chloro-4-methyl-2-imidazolinone, 1554 A -Chloro-5-methyl-2-oxazolidinone, 1488 A -Chloro-3 -morpholinone, 1489 A-Chloro-4-nitroaniline, 2231 A-Chloro-5-phenyltetrazole, 2674 A-Chloropiperidine, 1948 A -Chloropy rrolidine, 1584... 

Chlorine, positive , iodometric determination of, 48, 5 reaction with 2-butyne, 46, 34 a-Chloroacetamide, reaction with oxalyl chloride to give a-chloroacetyl isocyanate, 46, 16... 

Base-catalyzed cyclization of A -benzoyl-a-chloroacetamide is a classical method used to prepare 2-phenyl-4(5//)-oxazolone. Extension of this methodology to the A -aroylcinnamides 35 afforded a series of 5-arylidene analogues 37 albeit in unstated yield (Scheme 6.12). " Thus, acylation of the sodium salt of a benzamide with a cinnamoyl chloride gave the imides 35 that were converted to 36 via a bromination-dehydrobromination sequence. Cyclization to 37 was affected with sodium hydride in 1,2-dimethoxyethane (DME). The authors noted that catalytic reduction of 37 afforded the 5-(arylidene)oxazolidine from which 37 could be regenerated in the presence of air. 

From carboxylic acids a-Chloroacetamide, 70 Diazomethane-Alumina, 14 Diphenyldiazomethane, 242 Potassium hydroxide, 258 From other starting materials I-Butyl perbenzoate, 58 Dibromomethyllithium, 93 Di-p,-carbonylhexacarbonyldicobalt, 99... 

The a-chloroacetamide was obtained from Eastman Kodak Co and used without purification. 

Scheme 16 Preparation of spiroazetidin-2-ones through n-Bu3SnH mediated cyclization of a-chloroacetamide...

Erythrina alkaloids, possessing curare-like activity, are a large class of natural products found in Erythrina plants (Leguminosae). In a study towards construction of the erythrina skeleton, disfavored 5-endo-trig cyclizations were achieved by Ikeda et al. by BusSnH-mediated radical cyclization of an //-vinylic a-chloroacetamide to give five-membered lactams... 

Over a decade ago, work on the enzyme aldolase reductase elegantly demonstrated this point. The noncovalent inhibitor alrestatin was modified to contain various electrophiles a-chloroacetamide, a-bromoacetamide or a-iodoacetamide. Noncovalent interactions between inhibitors and protein would not have changed, but molecules behaved differently based on the electrophile the weakest showed reversible inhibition, whereas the iodoacetamide displayed almost complete irreversible inhibition.1401 These results are an important warning if a reaction is too facile, irreversible reactions can obscure true binding affinities. 

The a-chloroacetamide group has features that are beneficial for undirected ABPP. Its small size does not bias binding elements towards a specific class of enzyme, and it possesses reactivity towards a broad variety of nucleophilic amino acid residues. A library of a-chloroacetamide-based probes were synthesized by Cravatt s group. The binding element in these probes was a dipeptide that was varied with small, large, hydrophobic, and charged side chains, and a biotin or rhodamine tag was appended as a reporter tag. Upon screening of eukaryotic proteomes with this library, many enzymes previously unaddressed by directed ABPP probes were uncovered. These included fatty acid synthase, hydro-xypyruvate reductase, malic enzyme, and the nitrilase superfamily [163, 164]. In contrast to the sulfonate esters, a-chloroacetamides react preferentially with cysteine residues in the proteome. 

A key intermediate in the synthesis of pretazettine (Eq. 8), an alkaloid that contains a ds-3a-arylhydroindole ring system and shows antiviral and anticancer properties, has been synthesized by chlorine-atom transfer cyclization of a chloroacetamide in a highly stereocontrolled manner [25]. 

An example of the differentiation of diastereotopic hydrogens occurs in the formation of a /8-lactam, 60, from an optically active A-methylbenzyl-A-chloroacetamide acetonitrile, 59. When the starting chiral compound was (-t-)-R-a-(l-... 

CHLOROACETALDEHYDE see CDY500 CHLOROACETALDEHYDE MONOMER see CDY500 CHLOROACETAMIDE see CDY850 2-CHLOROACETAMIDE see CDY850 a-CHLOROACETAMIDE see CDY850... 

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