Development of an SNAr Reaction: A Practical and Scalable Strategy To Sequester and Remove HF

ORGANIC CHEMISTRY SELECT

A simple and operationally practical method to sequester and remove fluoride generated through the S_NAr reaction between amines and aryl fluorides is reported. Calcium propionate acts as an inexpensive and environmentally benign in situ scrubber of the hydrofluoric acid byproduct, which is simply precipitated and filtered from the reaction mixture during standard aqueous workup. The method has been tested from 10 to 100 g scale of operation, showing >99.5% decrease in fluoride content in each case. Full mass recovery of calcium fluoride is demonstrated at both scales, proving this to be a general, efficient, and robust method of fluoride abstraction to help prevent corrosion of glass-lined reactors.

A. John Blacker*^† , Gabriel Moran-Malagon^†, Lyn Powell^‡, William Reynolds^†, Rebecca Stones^†, and 

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Development of an SNAr Reaction: A Practical and Scalable Strategy To Sequester and Remove HF

A simple and operationally practical method to sequester and remove fluoride generated through the S_NAr reaction between amines and aryl fluorides is reported. Calcium propionate acts as an inexpensive and environmentally benign in situ scrubber of the hydrofluoric acid byproduct, which is simply precipitated and filtered from the reaction mixture during standard aqueous workup. The method has been tested from 10 to 100 g scale of operation, showing >99.5% decrease in fluoride content in each case. Full mass recovery of calcium fluoride is demonstrated at both scales, proving this to be a general, efficient, and robust method of fluoride abstraction to help prevent corrosion of glass-lined reactors.

A. John Blacker*^† , Gabriel Moran-Malagon^†, Lyn Powell^‡, William Reynolds^†, Rebecca Stones^†, and Michael R. Chapman^†

^† Institute of Process Research and Development, School of Chemistry and School of Chemical and Process Engineering, University of Leeds, Leeds LS2 9JT, United Kingdom

^‡ Chemical Development, AstraZeneca, Macclesfield SK10 2NA, United Kingdom

Org. Process Res. Dev., Article ASAP

DOI: 10.1021/acs.oprd.8b00090

*E-mail: j.blacker@leeds.ac.uk.

///////////////aryl amines, calcium fluoride, fluoride sequestration, scale-up, S_NAr reaction,

“ALL FOR DRUGS” CATERS TO EDUCATION GLOBALLY, No commercial exploits are done or advertisements added by me. This is a compilation for educational purposes only. P.S. : The views expressed are my personal and in no-way suggest the views of the professional body or the company that I represent

National award to Anthony Melvin Crasto for contribution to Pharma society from Times Network for Excellence in HEALTHCARE) | 5th July, 2018 | Taj Lands End, Mumbai, India

DR ANTHONY MEVIN CRASTO Conferred prestigious individual national award at function for contribution to Pharma society from Times Network, National Awards for Marketing Excellence ( For Excellence in HEALTHCARE) | 5th July, 2018 | Taj Lands End, Mumbai India

 

////////////National award,  contribution to Pharma society, Times Network, Excellence in HEALTHCARE,  5th July, 2018, Taj Lands End, Mumbai,  India, ANTHONY CRASTO

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National award to Anthony Melvin Crasto for contribution to Pharma society from Times Network for Excellence in HEALTHCARE) | 5th July, 2018 | Taj Lands End, Mumbai, India

New Drug Approvals

DR ANTHONY MEVIN CRASTO Conferred prestigious individual national award at function for contribution to Pharma society from Times Network, National Awards for Marketing Excellence ( For Excellence in HEALTHCARE) | 5th July, 2018 | Taj Lands End, Mumbai India

 

////////////National award,  contribution to Pharma society, Times Network, Excellence in HEALTHCARE,  5th July, 2018, Taj Lands End, Mumbai,  India, ANTHONY CRASTO

#hotpersoninawheelchair
#worlddrugtracker

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(1) Lawesson’s reagent 1956 — ChemInfoGraphic

via (1) Lawesson’s reagent 1956 — ChemInfoGraphic

Pidotimod, 匹多莫德 , пидотимод , بيدوتيمود ,

New Drug Approvals

Pidotimod

H-Pyr-Thz-OH

(4R)-3-[(2S)-5-oxopyrrolidine-2-carbonyl]-1,3-thiazolidine-4-carboxylic acid

CAS 121808-62-6

Thymodolic acid, Pidotimod, Timodolic acid, PGT/1A, Axil, Onaka, Pigitil, Polimod

(4R)-3-(5-oxo-L-prolyl)-l ,3-thiazolidine-4-carboxylic acid,  ITI 231723.

3-(L-pyroglutamyl)-L-thiazolidine-4-carboxylic acid

• 4-Thiazolidinecarboxylic acid, 3-[(5-oxo-2-pyrrolidinyl)carbonyl]-, [R-(R*,S*)]-
• (4R)-3-[[(2S)-5-Oxo-2-pyrrolidinyl]carbonyl]-4-thiazolidinecarboxylic acid
• Adimod
• Axil (pharmaceutical)
• Pigitil

QA-7522

SMR000466390

Thymodolic acid

Timodolic acid

UNII:785363R681

Pidotimod; 121808-62-6; (R)-3-((S)-5-Oxopyrrolidine-2-carbonyl)thiazolidine-4-carboxylic acid; Pidotomod; PGT/1A; Pidotimod [INN];
Molecular Formula:	C9H12N2O4S
Molecular Weight:	244.26758 g/mol

Stefano Poli, Corona Lucio Del

POLI INDUSTRIA CHIMICA S.p.A.

Pidotimod is an immunostimulant.^[1]

 

Pidotimod, whose chemical name is (4R)-3-(5-oxo-L-prolyl)-l ,3-thiazolidine-4-carboxylic acid, was first disclosed in ITI 231723. It is a synthetic peptide-like molecule provided with an in vitro and in vivo immunomodulating action (Giagulli et al., International Immunopharmacology, 9, 2009, 1366-1373). The immune system assists in maintaining a homeostatic balance between the human body and all foreign substances. An abnormality in this balance may cause a defective or aberrant response towards non-self substances…

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4,4,5,5-Tetramethyl-2-phenethyl-1,3,2-dioxaborolane — ORGANIC SPECTROSCOPY INTERNATIONAL

New Drug Approvals

4,4,5,5-tetramethyl-2-phenethyl-1,3,2-dioxaborolanehttp://orgsyn.org/demo.aspx?prep=v94p0234 4,4,5,5-Tetramethyl-2-phenethyl-1,3,2-dioxaborolane (1) has the following physical and spectroscopic properties: Rf = 0.47 (3:97, ethyl acetate:pentane), the checkers report the following values for 1: Rf = 0.09 (3:97 ethyl acetate:pentane); Rf = 0.52 (10% EtOAc in hexanes); Merck silica gel 60 F254 plate; mp 38-39 °C; 1H NMR pdf(CDCl3, 400 MHz) δ: 1.18 (t, J = 8.4 Hz, 2H), 1.26 (s, 12H), 2.79 (t, J = 8.0 Hz, 2H), 7.16-7.22 (m,…

via 4,4,5,5-Tetramethyl-2-phenethyl-1,3,2-dioxaborolane — ORGANIC SPECTROSCOPY INTERNATIONAL

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