19434-64-1Relevant articles and documents
Practical and efficient synthesis of N-halo compounds
Zhong, Yong-Li,Zhou, Hua,Gauthier, Donald R.,Lee, Jaemoon,Askin, David,Dolling, Ulf H.,Volante, Ralph P.
, p. 1099 - 1101 (2005)
A practical and efficient synthesis of N-halo compounds is described. Treatment of primary and secondary amines or amides with sodium hypohalite in the presence of tert-butanol and acetic acid afforded N-halo compounds in 90-100% yield.
New protocol for efficient N-chlorinations of amides and carbamates
Larionov, Oleg V.,Kozhushkov, Sergei I.,De Meijere, Armin
, p. 1916 - 1919 (2003)
N-Chlorination of various amides, carbamates and lactams with inexpensive and stable calcium hypochlorite on moist alumina proceeds smoothly and efficiently, e.g. the technically important 1-chlorohexahydroazepin-2-one (3-Cl) and 1-chloropyrrolidin-2-one (7-Cl) were obtained in 95 % and 98% yield, respectively. Excellent results were also observed for the N-chlorination of protected amino acid esters with a cyclopropane moiety to give derivatives such as methyl (tert-butoxycarbonylchloroamino)cyclopropylacetate (1-Cl), methyl (benzyloxycarbonylchloroamino)cyclopropylacetate (2-Cl), methyl 1-(tert-butoxycarbonylchloroamino)cyclopropanecarboxylate (5-Cl) and methyl trans-2-(tert-butoxycarbonylchloroamino)cyclopropanecarboxylate (6-Cl) in 99%, 96%, 90% and 97% yield, respectively.
PROCESS FOR ASYMMETRIC SYNTHESIS OF HEXAHYDROPYRIMIDO[1,2-A] AZEPINE-2-CARBOXAMIDES AND RELATED COMPOUNDS
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Page/Page column 36; 38, (2010/11/08)
Processes for asymmetric synthesis of 1O(S)-amino-3-hydroxy-4-oxo-4,6,7,8,9,10-hexahydropyrimido[1,2-a]azepine-2-carboxamides and related compounds are disclosed. The enantiomerically enriched carboxamides are useful as HIV integrase inhibitors and thus are useful for treating HIV infection and AIDS.
Ring contraction of N-chlorolactams, a novel rearrangement
Drouin, Alexandre,Lessard, Jean
, p. 4285 - 4288 (2007/10/03)
Upon photolysis in methylene chloride at -78 °C, different N-chlorolactams underwent a novel ring contraction to the corresponding carbamoyl chlorides, which were converted to the methyl carbamates. The rearrangement is 100% stereoselective, occurring with retention of configuration at the migrating carbon center. The yields of isolated carbamates ranged from 40% to 57%, the other product being the parent lactam, 18% to 38%.