Propionamide, 2-bromo

Figure 5-4. 2-Bromo-2-bromomethylglutaronitrile, 2,2-dibromo-3-nitrilo-propionamide, 1,2-dimethyl-5-nitro-1 H-imidazole, 4,4-dimethyl-2-oxazo-lidinone, dimethylaminopropyl acrylamide, dimethylaminopropyl methacrylamide, or dimethylaminopropyl acrylamide, 5,5-dimethylhydantoin, dimethylurea.

Methyleneazetidones have been obtained [39, 40] under liquiddiquid and solidrliquid basic conditions (Table 5.19) from an intramolecular cyclization and elimination reaction of 3-bromo-2-(bromomethyl)propionamides (Scheme 5.9). Traditional methods for the preparation of such compounds are either not particularly adaptable for general use, or involve lengthy and vigorous reaction conditions. In... 

Method A Using procedure 5.2.12.A, the 3-bromo-(2-bromomethyl)propionamide is stirred in aqueous NaOH (40%) and CCl4 (or CH2Cl2) in the presence of TEB A-Br or TEPA-Br for 18 h at room temperature to produce the azetidone. 

Fig. 4.10. (A) The chiral stationary phases (S)-naproxen-derived and (3R,4S)-Whelk 0 1. (B) CEC enantiomeric separation of an antidepressant (N-[l-(4-bromo-phenyl)-ethyl]-2,2-dimethyl-propionamide) on a column packed with (3R,4S)-Whelk-0 1 chiral phase immobilized on 3 pm silica. Adapted from ref. [79] with permission. Copyright Elsevier 1997.

The Step 6 pyridine derivative of the current invention, N-(5-bromo-pyridin-2-yl)-3-cyclopentyl-2-[3-fluoro-4-(5-methyl-tetrazol-l-y l)-phenyl]-propionamide, (I), was prepared by the author in a previous investigation (1). 

SYNS 3-BROMO-N-(2-CHLOROMERCURICYCLOHEX-YL)PROPIONAMIDE MERCURY (E)-CHLORO(2-(3-BROMOPROPIONAMIDO)-CYCLOHEXYL)... 

Nitro-4-(trifluoromethyl)-phenol 42 (Scheme 17) in reaction with 2-bromo-2-methyl-propionamide in the presence of cesium carbonate and cesium iodide in acetonitrile afforded 2-hydroxy-2-methylpropionamide 43, apparently via derivative 44 as the intermediate [32]. Amide 44, prepared on a circuitous route, on reduction with borane-dimethylsulfide complex, gave amine 45 as the only isolated product. The parent 2-hydroxy-2-methyl-W-(2-... 

Section II.7 describes some ring closures of the C-C-N-C-C, N-C-C-N-C-C, and N-C-C-N-C-C-N systems to give hydroxypyrazines (248, 365a, 477, 479, 480-483) more information can be found in reference 1054. Newbold and Spring (89) described the reaction of 2-bromo-A -(r-methyl-2 -oxopropyl)propionamide with ethanolic ammonia to give 2-hydroxy-3,5,6-trimethylpyrazine and Masaki et al. (551) have described the reaction of A -leucyl-6>-benzyIhydroxylamine (2) with phenacyl bromide in methanol saturated with ammonia to give 3-hydroxy-2-isobutyl-5-phenylpyrazine and 2,5-diphenylpyrazine. 

It can be prepared by a modification of Theilig s method (1953), by reaction of l-bromo-2-propanone (bromoacetone) and propionamide. 

It can be prepared by the general procedure of Theilig (1953) by reaction of 3-bromo-2-butanone with propionamide. 

Nitrophenol 141 during alkylation with 2-bromo-2-methylpropionic acid ethyl ester in the presence of cesium carbonate in acetonitrile underwent Smiles rearrangement to afford the corresponding propionamide 142. Further upon reduction of 144, which was obtained from 141 in a three step reaction, with borane dimethyl sulfide complex in THF, a Smiles rearrangement was observed furnishing the propanol 146. ... 

The phase-transfer-catalysed cyclization of 3-bromo-2-(bromomethyl)-propionamides provides a simple synthesis of a-methylene-/8-lactams (Scheme 89).The synthesis of 4-unsubstituted monocyclic /3-lactams has... 

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