Studies on ketene and its derivatives. LXXXV. Reactions of 4-bromo-3-hydroxybutanoate and its acyl derivatives.

doi:10.1248/CPB.25.2692

Paper

Studies on ketene and its derivatives. LXXXV. Reactions of 4-bromo-3-hydroxybutanoate and its acyl derivatives.

Published Oct 25, 1977 · Tetsuzo Kato, H. Kimura

Chemical & Pharmaceutical Bulletin

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5

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Abstract

Acylation of ethyl 4-bromo-3-hydroxybutanoate (I) with acetic anhydride, benzoyl chloride, diketene, and phenyl isocyanate gave rise to ethyl 3-acetoxy-4-bromobutanoate (IIa), ethyl 3-benzoyloxy-4-bromobutanoate (IIb), ethyl 3-acetoacetoxy-4-bromobutanoate (IIc), and ethyl 4-bromo-3-(N-phenylcarbamoyloxy) butanoate (IId), respectively. Reaction of IIa with sodium ethoxide in abs. ethanol gave ethyl 4-hydroxycrotonate (III) and ethyl 4-bromocrotonate (IV). The similar reaction of IIb afforded IV and 4-benzoyloxycrotonate (Vb). Similarly, IIc was converted to III, 4-acetoacetoxycrotonate (Vc), and 3-acetyl-4-ethoxycarbonylmethyltetrahydrofuran-2-one (VI). On the other hand, reaction of IId under the same condition did not give the acyl migrated product such as ethyl 4-N-phenylcarbamoyloxycrotonate (Vd) but afforded ethyl 4-anilinocrotonate (VIII).

Study Snapshot

Ethyl 4-bromo-3-hydroxybutanoate can be converted into various acyl derivatives, with ethyl 4-anilinocrotonate being the most promising product for pharmaceutical applications.

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

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Paper

Studies on ketene and its derivatives. LXXXV. Reactions of 4-bromo-3-hydroxybutanoate and its acyl derivatives.

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References

Citations

Purification and characterization of NADPH-dependent aldo–keto reductase specific for β-keto esters from Penicillium citrinum, and production of methyl (S)-4-bromo-3-hydroxybutyrate

The novel -keto ester reductase (KER) from Penicillium citrinum efficiently produces methyl (S)-4-bromo-3-hydroxybutyrate with high stereospecificity and high productivity in E. coli cells.

An endogenous sleep-inducing compound is a novel competitive inhibitor of fatty acid amide hydrolase.

OBr, an endogenous compound found in human cerebrospinal fluid, may be a physiological regulator of fatty acid amide levels and FAAH activity.