Analytical Chiral SFC. Application Guide 1

Transcription

1 Analytical Chiral SFC Application Guide 1

2 Introduction In the 1960s, University of Utah Professor J. Calvin Giddings discovered the phenomenon of supercritical fluid chromatography (SFC). Nearly 20 years later, Suprex, Inc., unveiled the first commercialized SFC analytical instrument with great fanfare. Initially, the technique did not catch on. Now in the 21st Century, pharmaceutical companies realize the tremendous time and cost savings of SFC chiral separations. SFC is becoming a very accepted technique for analytical through preparative separations. Papers presented at international symposia such as SPICA, CPhI, Prep, ACS, EAS, and Pittcon, show that SFC separations are faster, show better resolution, and use less solvent than conventional methods. Furthermore, CO 2 is a green solvent and is not flammable or hazardous. Super and sub-critical CO 2 modified with MeOH and other solvents outperforms normal-phase HPLC because the flow rates are typically five times faster without losing resolution. This speed advantage is due to unique CO 2 characteristics such as low viscosity, high diffusivity and low surface tension. SFC is an ideal preparative chromatography technique due to the vaporization of the CO 2 at the end of the preparative process, which reduces solvent removal costs. Thus, when using preparative SFC, the chemist actually requires far less equipment, columns, and post-chromatographic facilities meaning that the capital and operating costs are far lower. We hope you enjoy this sampling of applications on the Thar SFC Method Station using Regis Technologies columns.

3 Index of Compounds Abscisic Acid... 3 Acenaphthenol Acetoxychavicol-Acetate... 3 Althiazide Anthryl-Trifluoromethyl Carbinol ,1 -Bi-2-Naphthol... 3 Bendroflumethiazide... 4 ß-Blocker... 4 Bupivacaine... 4 Carprofen... 4 Chlorflurecol Methyl Ester... 4 Chlormezanone Chloromandelic Acid Chloromandelic Acid... 5 Coumachlor... 5 Cromakalim... 5 Devrinol... 5 Diclofop Methyl... 5 Diperodon... 6 Ethotoin... 6 Etodolac... 6 Fenoprofen... 6 Flurbiprofen... 6 Hydrobenzoin... 6 Ibuprofen... 7 Ifenprodil... 7 Indapamide... 7 Indoprofen... 7 Ketoprofen... 7 Ketorolac... 7 ß-Lactam... 8 Lansoprazole... 8 Leptophos... 8 Loxoprofen... 8 Luciferin... 8 Mandelic Acid... 8 Metalaxyl... 9 Methadone... 9 α-methoxyphenyl-acetic Acid... 9 Metolazone... 9 Modafinil... 9 Mosapride... 9 Nadifloxacin Nadolol Naproxen Nimodipine Omeprazole Permethrin Phosphine Oxides Phosphine Selenium-Oxide Pindolol Proglumide Propranolol Resmethrin trans-stilbene Oxide Sulfinpyrazone Sulfoxides Sulindac Suprofen Temazepam Tetrahydrobenzo(a)-pyrene-7-ol Tetrahydropalmatine Tetramethrin Tetramisole Thalidomide (Trifluoromethyl) -Mandelic Acid α-trityl-2-naphthalene Propionic Acid Troger s Base Trolox Tropicamide Vanilmandelic Acid Warfarin Zopiclone... 15

4 Abscisic Acid Acenaphthenol 1-Acetoxychavicol Acetate Althiazide 9-Anthryl Trifluoromethyl Carbinol 1,1 -Bi-2-Naphthol 3 SFC Chiral Application Guide I

5 Bendroflumethiazide Beta-Blocker Bupivicaine Carprofen Chlorflurecol Methyl Ester Chlormezanone SFC Chiral Application Guide I 4

6 2-Chloromandelic Acid 4-Chloromandelic Acid Coumachlor Cromakalim Devrinol, (Napropamide) Diclofop Methyl 5 SFC Chiral Application Guide I

7 Diperodon Ethotoin Etodolac Fenoprofen Flurbiprofen Hydrobenzoin SFC Chiral Application Guide I 6

8 Ibuprofen Ifenprodil Indapamide Indoprofen Ketoprofen Ketorolac 7 SFC Chiral Application Guide I

9 Beta-Lactam Lansoprazole Leptophos Loxoprofen Luciferin Mandelic Acid SFC Chiral Application Guide I 8

10 Metalaxyl Methadone α-methoxyphenyl Acetic Acid Metolazone Modafinil Mosapride 9 SFC Chiral Application Guide I

11 Nadifloxacin Nadolol Naproxen Nimodipine Omeprazole cis,trans-permethrin SFC Chiral Application Guide I 10

12 Phosphine Oxide #1 Phosphine Oxide #2 Phosphine Oxide #3 Phosphine Selenium Oxide Pindolol Proglumide 11 SFC Chiral Application Guide I

13 Propranolol Resmethrin trans-stilbene Oxide Sulfinpyrazone Sulfoxide #1 Sulfoxide #2 SFC Chiral Application Guide I 12

14 Sulfoxide #3 Sulfoxide #4 Sulindac Suprofen Temazepam Tetrahydrobenzo(a)pyrene-7-ol 13 SFC Chiral Application Guide I

15 Tetrahydropalmatine Tetramethrin Tetramisole Thalidomide 4-Trifluoromethyl Mandelic Acid α-trityl-2-naphthalene Propionic Acid SFC Chiral Application Guide I 14

16 Troger s Base Trolox Tropicamide Vanilmandelic Acid Warfarin Zopiclone 15 SFC Chiral Application Guide I

17 Regis HPLC Chiral Column Product List PRODUCT PARTICLE SIZE COLUMN DIMENSIONS PRODUCT# (R,R)-Whelk-O 1 5 µm, 100 Å 25 cm x 4.6 mm (R,R)-Whelk-O 1 5 µm, 100 Å 25 cm x 10.0 mm (R,R)-Whelk-O 1 5 µm, 100 Å 25 cm x 30.0 mm (S,S)-Whelk-O 1 5 µm, 100 Å 25 cm x 4.6 mm (S,S)-Whelk-O 1 5 µm, 100 Å 25 cm x 10.0 mm (S,S)-Whelk-O 1 5 µm, 100 Å 25 cm x 30.0 mm (R,R)-Whelk-O 1 10 µm, 100 Å 25 cm x 4.6 mm (R,R)-Whelk-O 1 10 µm, 100 Å 25 cm x 10.0 mm (R,R)-Whelk-O 1 10 µm, 100 Å 25 cm x 21.1 mm (R,R)-Whelk-O 1 10 µm, 100 Å 50 cm x 21.1 mm (R,R)-Whelk-O 1 10 µm, 100 Å 25 cm x 30.0 mm (R,R)-Whelk-O 1 10 µm, 100 Å 25 cm x 50.0 mm (R,R)-Whelk-O 1 10 µm, 100 Å 50 cm x 30.0 mm (R,R)-Whelk-O 1 10 µm, 100 Å 50 cm x 50.0 mm (S,S)-Whelk-O 1 10 µm, 100 Å 25 cm x 4.6 mm (S,S)-Whelk-O 1 10 µm, 100 Å 25 cm x 10.0 mm (S,S)-Whelk-O 1 10 µm, 100 Å 25 cm x 21.1mm (S,S)-Whelk-O 1 10 µm, 100 Å 50 cm x 21.1 mm (S,S)-Whelk-O 1 10 µm, 100 Å 25 cm x 30.0 mm (S,S)-Whelk-O 1 10 µm, 100 Å 25 cm x 50.0 mm (S,S)-Whelk-O 1 10 µm, 100 Å 50 cm x 30.0 mm (S,S)-Whelk-O 1 10 µm, 100 Å 50 cm x 50.0 mm (R,R)-Whelk-O 2 10 µm, 100 Å 25 cm x 4.6 mm (R,R)-Whelk-O 2 10 µm, 100 Å 25 cm x 10.0 mm (R,R)-Whelk-O 2 10 µm, 100 Å 25 cm x 21.1 mm (R,R)-Whelk-O 2 10 µm, 100 Å 50 cm x 21.1 mm (R,R)-Whelk-O 2 10 µm, 100 Å 25 cm x 30.0 mm (R,R)-Whelk-O 2 10 µm, 100 Å 25 cm x 50.0 mm (R,R)-Whelk-O 2 10 µm, 100 Å 50 cm x 30.0 mm (R,R)-Whelk-O 2 10 µm, 100 Å 50 cm x 50.0 mm (S,S)-Whelk-O 2 10 µm, 100 Å 25 cm x 4.6 mm (S,S)-Whelk-O 2 10 µm, 100 Å 25 cm x 10.0 mm (S,S)-Whelk-O 2 10 µm, 100 Å 25 cm x 21.1mm (S,S)-Whelk-O 2 10 µm, 100 Å 50 cm x 21.1 mm (S,S)-Whelk-O 2 10 µm, 100 Å 25 cm x 30.0 mm (S,S)-Whelk-O 2 10 µm, 100 Å 25 cm x 50.0 mm (S,S)-Whelk-O 2 10 µm, 100 Å 50 cm x 30.0 mm (S,S)-Whelk-O 2 10 µm, 100 Å 50 cm x 50.0 mm (R,R)-ULMO 5 µm, 100 Å 25 cm x 4.6 mm (R,R)-ULMO 5 µm, 100 Å 25 cm x 10.0 mm (R,R)-ULMO 5 µm, 100 Å 25 cm x 30.0 mm (S,S)-ULMO 5 µm, 100 Å 25 cm x 4.6 mm (S,S)-ULMO 5 µm, 100 Å 25 cm x 10.0 mm (S,S)-ULMO 5 µm, 100 Å 25 cm x 30.0 mm (R,R)-ULMO 10 µm, 100 Å 25 cm x 21.1 mm (R,R)-ULMO 10 µm, 100 Å 25 cm x 30.0 mm (R,R)-ULMO 10 µm, 100 Å 25 cm x 50.0 mm (R,R)-ULMO 10 µm, 100 Å 50 cm x 30.0 mm (R,R)-ULMO 10 µm, 100 Å 50 cm x 50.0 mm (S,S)-ULMO 10 µm, 100 Å 25 cm x 21.1 mm (S,S)-ULMO 10 µm, 100 Å 25 cm x 30.0 mm SFC Chiral Application Guide I 16

18 Regis HPLC Chiral Column Product List (S,S)-ULMO 10 µm, 100 Å 25 cm x 50.0 mm (S,S)-ULMO 10 µm, 100 Å 50 cm x 30.0 mm (S,S)-ULMO 10 µm, 100 Å 50 cm x 50.0 mm (R,R)-DACH-DNB 5 µm, 100 Å 25 cm x 4.6 mm (R,R)-DACH-DNB 5 µm, 100 Å 25 cm x 10.0 mm (R,R)-DACH-DNB 5 µm, 100 Å 25 cm x 30.0 mm (S,S)-DACH-DNB 5 µm, 100 Å 25 cm x 4.6 mm (S,S)-DACH-DNB 5 µm, 100 Å 25 cm x 10.0 mm (S,S)-DACH-DNB 5 µm, 100 Å 25 cm x 30.0 mm (R,R)-DACH-DNB 10 µm, 100 Å 25 cm x 21.1 mm (R,R)-DACH-DNB 10 µm, 100 Å 25 cm x 30.0 mm (R,R)-DACH-DNB 10 µm, 100 Å 25 cm x 50.0 mm (R,R)-DACH-DNB 10 µm, 100 Å 50 cm x 30.0 mm (R,R)-DACH-DNB 10 µm, 100 Å 50 cm x 50.0 mm (S,S)-DACH-DNB 10 µm, 100 Å 25 cm x 21.1 mm (S,S)-DACH-DNB 10 µm, 100 Å 25 cm x 30.0 mm (S,S)-DACH-DNB 10 µm, 100 Å 25 cm x 50.0 mm (S,S)-DACH-DNB 10 µm, 100 Å 50 cm x 30.0 mm (S,S)-DACH-DNB 10 µm, 100 Å 50 cm x 50.0 mm (3R,4S)-Pirkle 1-J 5 µm, 100 Å 25 cm x 4.6 mm (3R,4S)-Pirkle 1-J 5 µm, 100 Å 25 cm x 10.0 mm (3S,4R)-Pirkle 1-J 5 µm, 100 Å 25 cm x 4.6 mm (3S,4R)-Pirkle 1-J 5 µm, 100 Å 25 cm x 10.0 mm (R,R)-α-Burke 2 5 µm, 100 Å 25 cm x 4.6 mm (R,R)-α-Burke 2 5 µm, 100 Å 25 cm x 10.0 mm (S,S)-α-Burke 2 5 µm, 100 Å 25 cm x 4.6 mm (S,S)-α-Burke 2 5 µm, 100 Å 25 cm x 10.0 mm (R,R)-β-Gem 1 5 µm, 100 Å 25 cm x 4.6 mm (R,R)-β-Gem 1 5 µm, 100 Å 25 cm x 10.0 mm (S,S)-β-Gem 1 5 µm, 100 Å 25 cm x 4.6 mm (S,S)-β-Gem 1 5 µm, 100 Å 25 cm x 10.0 mm D-Leucine 5 µm, 100 Å 25 cm x 4.6 mm D-Leucine 5 µm, 100 Å 25 cm x 10.0 mm L-Leucine 5 µm, 100 Å 25 cm x 4.6 mm L-Leucine 5 µm, 100 Å 25 cm x 10.0 mm D-Phenylglycine 5 µm, 100 Å 25 cm x 4.6 mm D-Phenylglycine 5 µm, 100 Å 25 cm x 10.0 mm L-Phenylglycine 5 µm, 100 Å 25 cm x 4.6 mm L-Phenylglycine 5 µm, 100 Å 25 cm x 10.0 mm L-Naphthylleucine 5 µm, 100 Å 25 cm x 4.6 mm L-Naphthylleucine 5 µm, 100 Å 25 cm x 10.0mm Bulk material is available for all Chiral Stationary Phases For column dimensions not listed, please contact Regis 17 SFC Chiral Application Guide I

19 Free Chiral Screening on HPLC and SFC Since the introduction of the first Pirkle Type Chiral HPLC column in 1980, Regis Technologies has been a recognized leading manufacturer of chiral stationary phases. The Regis team is dedicated to providing the best technical support as well as outstanding method development support for the resolution of chiral compounds. At Regis, we embrace new advances in separation technology. We recently installed an analytical SFC unit since we feel SFC is a promising technique. Regis now offers Free Chiral Screening in both HPLC and SFC. Our goal is to give you the best resolution method for your compound by identifying the best Pirkle-type column and separation technique based on your needs. This new SFC guide contains only a sample of the compounds separated on our columns using a Thar Method Station SFC. New methods are developed each month. For sales inquires, technical assistance and Free Chiral Screening information, please contact a Regis team member listed below: Mr. Francis Mannerino Ted Szczerba Director of Chromatography Division Technical Director Phone: Phone: Fax: Fax: fran@registech.com teds@registech.com Ms. Jelena Kocergin Andy Miles International Sales Manager Chiral Sales Specialist Phone: Phone: Fax: Fax: regisintl@registech.com amiles@registech.com Sean F. Bradley Hamilton Lenox Director of Business Development Manager of Sales Central Region Phone: Phone: Fax: Fax: sbradley@registech.com hlenox@registech.com Elena Chekhova, Ph.D. Deb Minor, Ph.D. Manager of Sales Eastern Region Sales Representative Phone: Phone: Fax: Fax: echekhova@registech.com sales@registech.com SFC Chiral Application Guide I 18

20 For Sales and Technical assistance: Phone: Fax: Regis Technologies,Inc 8210 Austin Ave. Morton Grove, IL 60053