Chemistry of carbon compounds – Miscellaneous organic carbon compounds – C-metal
Patent
1976-06-04
1978-04-04
Douglas, Winston L.
Chemistry of carbon compounds
Miscellaneous organic carbon compounds
C-metal
2604045, 1951035R, A23J 700, C07F 902
Patent
active
040827810
ABSTRACT:
A method for synthesizing a 2-alkanoylamino-4-nitrophenyl phosphorylcholine-hydroxide useful as a sphingomyelinase-specific chromogenic artificial substrate in the diagnostic testing for Niemann-Pick disease. The method comprises reacting 2-amino-4-nitrophenol with an alkanoyl halide to form the alkananilide; phosphorylating the alkali phenolate salt of the alkananilide with .beta.-bromoethylphosphoryl dichloride to form a mixture of mono- and di-alkananilide phosphoric acid esters; recovering from the mixture the mono-alkananilide phosphoric acid ester and quaternizing it with trimethylamine; and treating the resulting quaternary salt with a mixture of weak acidic and weak basic ion exchange resins to convert it into the 2-alkanoylamino-4-nitrophenyl phosphoryl-choline-hydroxide.
REFERENCES:
patent: 3531374 (1970-09-01), Brady et al.
patent: 3772360 (1973-11-01), Pfeiffer et al.
Brady, R. The American Journal of Medicine, vol. 51, Oct. 1971 pp. 423-431.
Buehler et al., Survey of Organic Synthesis, (1970) p. 899.
Morrison et al. Organic Chemistry, 3rd ed. (1973) p. 793.
Douglas Winston L.
Niebling John F.
The United States of America as represented by the Department of
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