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74 nitrosyl chloride, reaction with amides

The key reaction, based on a method for removing glutamate residues in peptides, involves the conversion of the sole primary amine in the molecule to a diazo function. The most expeditious method consists of reacting (18-1) with nitrosyl chloride. The resulting diazo function in the product (18-2) can be displaced formally by oxygen from the enol form of the amide at the 7 position to form the iminolactone (18-3) the reaction may involve a spontaneous loss of nitrogen followed by capture of the resulting carbocation. Hydrolysis of the imine function in the product the leads to one of the key intermediates in this series, 7-ACA (18-4) [22]. [Pg.558]

Nitrosamines. Nitrosamines are usually prepared by reaction of rec-amines with nitrous acid in water. They can also be prepared by conversion of tbe amine into the sodium amide (NaH, THF) followed by reaction with nitrosyl chloride. jcc-Amines also react directly with nitrosyl chloride in THF if pyridine is added as base. Yields by either method are fair to good. - R. E. Lyle, J. E. Saavedra, and G. G. Lyle, Synthesis, 462 (1976). [Pg.131]

The first effective method of side chain cleavage made use of the reaction of (179) with nitrosyl chloride (152). Loss of nitrogen from the intermediate diazo compound (181) gives imine (182) which on hydrolysis provides 7-ACA (180) and the lactone (183). This provided a route to substantial quantities of (180) thus allowing the preparation of many side chain derivatives. Later a more efficient procedure made use of phosphorus pentachloride followed by cleavage of an imino ether (153). The utility of other phosphorus halogen compounds for cleavage of the amide bond has also been described (154). [Pg.39]


See other pages where 74 nitrosyl chloride, reaction with amides is mentioned: [Pg.226]    [Pg.67]    [Pg.257]    [Pg.100]    [Pg.362]    [Pg.380]    [Pg.89]    [Pg.693]    [Pg.959]    [Pg.995]    [Pg.370]    [Pg.1014]    [Pg.2042]    [Pg.2041]   
See also in sourсe #XX -- [ Pg.41 , Pg.245 , Pg.274 ]




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Amidating reaction

Amidation reactions

Amide Reaction

Amide chlorides

Nitrosyl chlorid

Nitrosyl chloride

Nitrosyl chloride, reaction

Nitrosyl reaction

Nitrosyl reactions with

Reaction with amides

Reaction with nitrosyl chloride

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