Application of Oxathiazolidine-S-oxide Chemistry to the Large-Scale Single-Step Synthesis of an O-Arylethanolamine

Barker, A. J.; Boardman, Kay A.; Broady, Simon D.; Moss, William O.; Patel, Bharti; Senior, A; Warren, Kenneth E. H.

doi:10.1021/op9800865

Cited by 5 publications

(1 citation statement)

References 10 publications

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“…To this end, the β-substituted itaconate salt 17 was prepared via a Horner-Wadsworth-Emmons olefination, and it was found that this substrate could be hydrogenated (Scheme 4) using [(S)-BINAP-Ru-(p-cymene)Cl]Cl to give the product 16 in 88% ee Crystallization as the cyclohexylamine salt gave a purity of >98% ee and a 65% overall yield from itaconate 17. This olefination/hydrogenation approach therefore obviates the need for 22) (a beta-3 agonist) 32 entered development in 1991, intended for the treatment of noninsulin dependent diabetes. The medicinal chemistry route to 22 (Scheme 5) presented a number of challenges for scale-up.…”

Section: Removal Of a Potential Explosion Hazardmentioning

confidence: 99%

Critical Assessment of Pharmaceutical ProcessesA Rationale for Changing the Synthetic Route

et al. 2006

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Section: Removal Of a Potential Explosion Hazardmentioning

confidence: 99%

Critical Assessment of Pharmaceutical ProcessesA Rationale for Changing the Synthetic Route

et al. 2006

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ChemInform Abstract: Application of Oxathiazolidine‐S‐oxide Chemistry to the Large‐Scale Single‐Step Synthesis of an O‐Arylethanolamine.

et al. 1999

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Application of Oxathiazolidine-S-oxide Chemistry to the Large-Scale Single-Step Synthesis of an O-Arylethanolamine. -The synthesis of target amine (III) by O-alkylation of phenol (I) with the oxathiazolidine-S-oxide (II) instead with N-benzylethanolamine is successfully used for pilot plant manufacture. -(BARKER, ALAN C.; BOARDMAN, KAY A.; BROADY, SIMON D.; MOSS, WILLIAM O.; PATEL, BHARTI; SENIOR, MICHAEL W.; WARREN, KENNETH E. H.; Org. Process Res. Dev. 3 (1999) 4, 253-255; Proc. Dev. Dep., Zeneca Pharm., Macclesfield, Cheshire SK10 2NA, UK; EN)

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Diastereoselective Synthesis and Configurational Assignment of Novel Functionalized Cyclic Sulfamidites Precursors of Cyclic Sulfamidates

Slama

Arfaoui

Besbes

2016

Heteroatom Chemistry

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New 3,4,5‐trisubstituted sulfamidites were prepared through cyclization of β‐amino alcohol diesters with thionyl chloride. The oxidation of these N‐alkylated sulfamidites into the corresponding sulfamidates was then performed. Interestingly, the NMR spectra of the prepared sulfamidites revealed that the ratios of the exo and endo diastereomers of these compounds were influenced by the substituents on the α‐carbon. In addition, theoretical calculations at the DFT B3LYP/6‐31G(d) level were carried and indicated that the exo‐diastereomers were more stable than the endo forms.

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Application of Oxathiazolidine-S-oxide Chemistry to the Large-Scale Single-Step Synthesis of an O-Arylethanolamine

Abstract: Alternative routes to the arylethanolamine subunit of a development drug have been investigated. The selected route, involving O-alkylation of a phenol using N-benzyloxathiazolidine-S-oxide, was developed to give a process used successfully for pilot plant manufacture.

Cited by 5 publications

References 10 publications

Critical Assessment of Pharmaceutical ProcessesA Rationale for Changing the Synthetic Route

Critical Assessment of Pharmaceutical ProcessesA Rationale for Changing the Synthetic Route

ChemInform Abstract: Application of Oxathiazolidine‐S‐oxide Chemistry to the Large‐Scale Single‐Step Synthesis of an O‐Arylethanolamine.

Diastereoselective Synthesis and Configurational Assignment of Novel Functionalized Cyclic Sulfamidites Precursors of Cyclic Sulfamidates

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