N-Substituted trimethylsilylcarbamates as silylating and/or methoxime derivatizing reagents for gas chromatographic analysis

Knausz, D.; Meszticzky, A.; Rohonczy, János; Kolos, Zs; Csákvári, B.; Szederkényi, F.; Újszászy, Kálmán

doi:10.1016/s0021-9673(01)81555-7

Cited by 14 publications

(2 citation statements)

References 7 publications

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“…The reaction was improved by trapping the intermediate salt 31 in order to push the equilibrium towards completion. The use of trimethylsilyl chloride was found to be the right choice, leading to a higher conversion of the starting material and a less variable profile. The resulting hypothetical trimethylsilyl species 32 forced the equilibrium between salt 31 and starting material 16 (Scheme ), even when running the reaction at room temperature.…”

Section: Development Of a Convergent Processmentioning

confidence: 99%

Synthesis of the NK1 Receptor Antagonist GW597599. Part 3: Development of a Scalable Route to a Key Chirally Pure Arylpiperazine Urea, A Happy End

Guercio

Bacchi

Perboni

et al. 2009

Org. Process Res. Dev.

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GW597599 1 is a novel NK-1 antagonist currently under investigation for the treatment of central nervous system disorders and emesis. The initial chemical development synthetic route, derived from the one used by medicinal chemistry, involved several hazardous reagents, gave low yields and produced high levels of waste. Through a targeted process of research and development, application of novel techniques and extensive route scouting, a new synthetic route for GW597599 was developed. This paper reports the optimisation work of the third and last stage in the chemical synthesis of GW597599 and the development of a pilot-plant-suitable process for the manufacturing of optically pure arylpiperazine derivative 1. In particular, the process eliminated the use of triphosgene in the synthesis of an intermediate carbamoyl chloride, substantially enhancing safety, overall yield, and throughput.

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Section: Development Of a Convergent Processmentioning

confidence: 99%

Synthesis of the NK1 Receptor Antagonist GW597599. Part 3: Development of a Scalable Route to a Key Chirally Pure Arylpiperazine Urea, A Happy End

Guercio

Bacchi

Perboni

et al. 2009

Org. Process Res. Dev.

View full text Add to dashboard Cite

show abstract

“…A new reagent, N-methoxy--N,0--bis(trimethylsilyl) carbonate, allows the simultaneous formation of methoxime derivatives of ketone groups and silylation of hydroxyl groups [455]. Secondary products can be formed under normal conditions for silyl ether formation with compounds containing unprotected ketone groups.…”

Section: Derivatization Techniques For Gas Chromatographymentioning

confidence: 99%