Synthesis of an Alleged Byproduct Precursor in Iodixanol Preparation
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1 SUPPORTING INFORMATION Synthesis of an Alleged Byproduct Precursor in Iodixanol Preparation Marianne Bore Haarr, Emil Lindbäck, Torfinn Håland, * and Magne O. Sydnes * Department of Mathematics and Natural Sciences, University of Stavanger, NO-4036, Stavanger, Norway GE Healthcare, Lindesnes Site, NO-4521 Lindesnes, Norway * torfinn.haaland@ge.com * magne.o.sydnes@uis.no Spectra and Figures presented Figure. s1 Figure. s2 Figure. s Figure. s4 1 H NMR spectrum of 5-Acetamido-N 1,N 3 -bis(2,3-bis((tertbutyldimethylsilyl)oxyl)propyl)-2,4,6-triiodoisophthalamide (3) at 400 K 4 Figure. s5 1 H NMR spectrum of 5-Acetamido-N 1,N 3 -bis(2,3-bis((tertbutyldimethylsilyl)oxyl)propyl)-2,4,6-triiodoisophthalamide (3) 5 Figure. s6: 13 C NMR spectrum of 5-Acetamido-N 1,N 3 -bis(2,3-bis((tertbutyldimethylsilyl)oxyl)propyl)-2,4,6-triiodoisophthalamide (3) 6 Figure. s7 HSQC NMR spectrum of 5-Acetamido-N 1,N 3 -bis(2,3-bis((tertbutyldimethylsilyl)oxyl)propyl)-2,4,6-triiodoisophthalamide (3) 7
2 Figure. s8 1 H NMR spectrum of 5-(N-Allylacetamido)-N 1,N 3 -bis(2,3-bis((tertbutyldimethylsilyl)oxy)propyl)-2,4,6-triiodoisophthalamide (4) at 400 K 8 Figure. s9 1 H NMR spectrum of 5-(N-Allylacetamido)-N 1,N 3 -bis(2,3-bis((tertbutyldimethylsilyl)oxy)propyl)-2,4,6-triiodoisophthalamide (4) 9 Figure. s10 13 C NMR spectrum of 5-(N-Allylacetamido)-N 1,N 3 -bis(2,3-bis((tertbutyldimethylsilyl)oxy)propyl)-2,4,6-triiodoisophthalamide (4) 10 Figure. s11 1 H NMR spectrum of N 1,N 3 -bis(2,3-bis((tertbutyldimethylsilyl)oxy)propyl)-5-(n-(2,3-dihydroxypropyl) acetamido)-2,4,6- triiodoisophthalamide (5). 11 Figure. s12 13 C NMR spectrum of N 1,N 3 -bis(2,3-bis((tertbutyldimethylsilyl)oxy)propyl)-5-(n-(2,3-dihydroxypropyl) acetamido)-2,4,6- triiodoisophthalamide (5). 12 Figure. s13 HSQC NMR spectrum of N 1,N 3 -bis(2,3-bis((tertbutyldimethylsilyl)oxy)propyl)-5-(n-(2,3-dihydroxypropyl) acetamido)-2,4,6- triiodoisophthalamide (5). 13 Figure. s14 1 H NMR spectrum of 3-(N-(3,5-bis((2,3-bis((tert- butyldimethylsilyl)oxy)propyl)carbamoyl)-2,4,6-triiodophenyl)acetamido)-2- hydroxypropyl methanesulfonate (6). 14 Figure s15: 13 C NMR spectrum of 3-(N-(3,5-bis((2,3-bis((tert- butyldimethylsilyl)oxy)propyl)carbamoyl)-2,4,6-triiodophenyl)acetamido)-2- hydroxypropyl methanesulfonate (6). 15 Figure. s16 HSQC NMR spectrum of 3-(N-(3,5-bis((2,3-bis((tert- butyldimethylsilyl)oxy)propyl)carbamoyl)-2,4,6-triiodophenyl)acetamido)-2- hydroxypropyl methanesulfonate (6). 16 Figure. s17 1 H NMR spectrum of 3-(N-(3,5-bis((2,3-bis((tert- butyldimethylsilyl)oxy)propyl)carbamoyl)-2,4,6-triiodophenyl)acetamido)-1,2- dimethanesulfonate (8) 17
3 Figure. s18 HSQC NMR spectrum of 3-(N-(3,5-bis((2,3-bis((tert- butyldimethylsilyl)oxy)propyl)carbamoyl)-2,4,6-triiodophenyl)acetamido)-1,2- dimethanesulfonate (8) 18 Figure. s19 HMBC NMR spectrum of 3-(N-(3,5-bis((2,3-bis((tert- butyldimethylsilyl)oxy)propyl)carbamoyl)-2,4,6-triiodophenyl)acetamido)-1,2- dimethanesulfonate (8) 19 Figure. s20 1 H NMR spectrum of N 1,N 3 -bis(2,3-bis((tert- butyldimethylsilyl)oxy)propyl)-2,4,6-triiodo-5-(n-(oxiran-2- ylmethyl)acetamido)isophthalamide (7) 20 Figure. s21 13 C NMR spectrum of N 1,N 3 -bis(2,3-bis((tert- butyldimethylsilyl)oxy)propyl)-2,4,6-triiodo-5-(n-(oxiran-2- ylmethyl)acetamido)isophthalamide (7) 21 Figure. s22 HSQC NMR spectrum of N 1,N 3 -bis(2,3-bis((tert- butyldimethylsilyl)oxy)propyl)-2,4,6-triiodo-5-(n-(oxiran-2- ylmethyl)acetamido)isophthalamide (7) 22 Figure. s23 1 H NMR spectrum of N 1,N 3 -bis(2,3-dihydroxypropyl)-2,4,6- triiodo-5-(n-(oxiran-2-ylmethyl)acetamido) isophthalamide (1) 23 Figure. s24 13 C NMR spectrum of N 1,N 3 -bis(2,3-dihydroxypropyl)-2,4,6- triiodo-5-(n-(oxiran-2-ylmethyl)acetamido) isophthalamide (1) 24 Figure. s25 HSQC NMR spectrum of N 1,N 3 -bis(2,3-dihydroxypropyl)-2,4,6- triiodo-5-(n-(oxiran-2-ylmethyl)acetamido) isophthalamide (1) 25
4 Note: All NMR experiments were run with as close to saturated solutions of compound in d 6-DMSO as possible. Solubility in d 6-DMSO could explain variability in the observation of aromatic peaks in 13 C NMR spectra. High temperature NMR could help evaluate the observations, however long run times due to number of scans necessary to produce the 13 C NMR spectra made high temperature NMR not feasible with the equipment available.
5 Figure. s1 Components of the reaction mixture during preparation of iodixanol. S mv = 254, Rng = , Rsp = 1.0, St = 0.20, Avg = On, Az Amide 2 (endo) Amide 2 (exo) Iohexol (endo) Iohexol (exo) Epoxide min WVL:254 nm Iodixanol (split peaks due to endo/endo, endo/exo, and exo/exo rotational isomerism)
6 Figure. s2 HPLC chromatogram of synthesized epoxide 1 and ring opening product iohexol. S mau 40.0 Iohexol (endo) Iohexol (exo) Epoxide min
7 S3 a b endo exo exo endo c d exo endo Figure. s3 Endo/exo configuration of compound 3 at 298 K (a) and 400 K (c), and of compound 4 at 298 K (b) and 400 K (d) identified by the compounds methyl group 1 H NMR signal.
8 S4 400K ppm Figure. s4 1 H NMR spectrum of compound 3 recorded at 400 K DMSO-d6
9 S ppm Figure. s5 1 H NMR spectrum of compound 3 recorded at rt (DMSO-d6 400 MHz)
10 S ppm Figure. s6 13 C NMR spectrum of compound 3 (DMSO-d6 100 MHz)
11 S7 ppm ppm Figure. s7 HSQC NMR spectrum of compound 3 (DMSO-d6 100 MHz)
12 S8 400K ppm Figure. s8 1 H NMR spectrum of compound 4 recorded at 400 K (DMSO-d6 400 MHz)
13 S ppm Figure. s9 1 H NMR spectrum of compound 4 recorded at rt (DMSO-d6 400 MHz)
14 S ppm Figure. s10 13 C NMR spectrum of compound 4 (DMSO-d6 100 MHz)
15 S ppm Figure. s11 1 H NMR spectrum of compound 5 (DMSO-d6 400 MHz)
16 S ppm Figure. s12 13 C NMR spectrum for compound 5 (DMSO-d6 100 MHz)
17 S13 ppm ppm Figure. s13 HSQC NMR spectrum for compound 5 (DMSO-d6 100 MHz)
18 S ppm Figure. s14 1 H NMR spectrum for compound 6 (DMSO-d6 400 MHz)
19 S15 ppm ppm Figure. s15 HSQC NMR spectrum for compound 6 (DMSO-d6 100 MHz)
20 S16 ppm ppm Figure. s 16 HMBC NMR spectrum for compound 6 (DMSO-d6 100 MHz)
21 S ppm Figure. s 17 1 H NMR spectrum for compound 8 (DMSO-d6 400 MHz)
22 S ppm Figure. s18 13 C NMR spectrum for compound 8 (DMSO-d6 100 MHz)
23 S19 ppm ppm Figure. s19 HSQC NMR spectrum for compound 8 (DMSO-d6 100 MHz)
24 S ppm Figure. s20 1 H NMR spectrum for compound 7 (DMSO-d6 400 MHz)
25 S ppm Figure. s21 13 C NMR spectrum for compound 7 (DMSO-d6 100 MHz)
26 S22 ppm ppm Figure. s22 HSQC NMR spectrum for compound 7 (DMSO-d6 100 MHz)
27 S ** * * * ppm Figure. s23 1 H NMR spectrum for compound 1 (DMSO-d6 400 MHz) (*residual ethyl acetate, **residual acetone)
28 S ** ** * * * ppm Figure. s24 13 C NMR spectrum for compound 1 (DMSO-d6 100 MHz) (*residual ethyl acetate, **residual acetone)
29 S25 ppm ppm Figure. s25 HSQC NMR spectrum for compound 1 (DMSO-d6 100 MHz)
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