143  US 9,904,167 B2  144  Q  CC SX)~  0  #  Compound (for Examples)  Chemical Formula  Compound (Al)  TABLE 1  3.92 g of amino methanesulfonic acid and 10.45 g of  triphenylsulfonium bromide was changed to 10.88 g of the  following sulfonium salt.  10.1 g of the compound (AlO) was obtained with the same  method as in the synthesis of the compound (A3) except that 15  the 6.05 g of adamantane carbonyl chloride was changed to  3.67 g of pivaloyl chloride.  $^{1}$H-NMR (400 MHz, d6-DMSO) 0=7.89-7.76 (15H, m),  7.64 (lH, brs), 3.31 (m, 2H), 2.55 (t, 2H), 1.06 (s, 9H)  10.3 g of the compound (All) was obtained with the same  method as in the synthesis of the compound (Al) except that  the 6.05 g of adamantane carbonyl chloride was changed to  4.27 g of benzoyl chloride.  $^{1}$H-NMR (400 MHz, D 2 O) o=7.98 (d, 2H), 7.80-7.63 (m,  17H), 7.55 (t, 2H), 3.11-3.06 (2H, m), 3.02-2.97 (2H, m)  21.4 g of phthalic anhydride, 17 g of taurine, and 14.2 g  of potassium acetate were added to 48 mL of acetic acid and  stirred while carrying out refluxing for 2.5 hours. After  cooling to 0°  C. after the reaction and filtering the precipi› tate, spray washing was carried out with acetic acid and  ethanol. Next, after adding the obtained crystals to a metha› nol solution of 38.6 g of triphenylsulfonium bromide and  stirring for 30 minutes at room temperature, separation was  carried out by adding pure water and ethyl acetate to the  reaction mixture and the organic phase was cleaned with  pure water, then the compound (A12) (52.3 g) was obtained  by vacuum drying after distilling off the solvent under  reduced pressure.  $^{1}$H-NMR (400 MHz, D2O) o=7.85 (4H, m), 7.80-7.63 (m,  15H), 4.05 (2H, t), 3.25 (2H, t)  13.3 g of the compound (A13) was obtained with the same  method as in the synthesis of the compound (A3) except that  the 10.45 g of triphenylsulfonium bromide was changed to  10.67 g of the following iodonium salt.  $^{1}$H-NMR (400 MHz, CDC1$_{3}$ )  o=7.91 (d, 4H), 7.57 (t, 2H),  7.41 (t, 4H), 3.71-3.66 (m, 2H), 2.93-2.89 (m, 2H), 1.98- 1.62 (m, 15H)  10.2 g of the compound (A14) was obtained with the same  method as in the synthesis of the compound (A3) except that  the 6.05 g of adamantane carbonyl chloride was changed to  5.38 g of benzenesulfonyl chloride.  10.3 g of the compound (A15) was obtained with the same 65  method as in the synthesis of the compound (A3) except that  the 4.42 g of 2-aminoethanesulfonic acid was changed to  10.8 g of the compound (A16) was obtained with the same  method as in the synthesis of the compound (A3) except that  the 4.42 g of 2-aminoethanesulfonic acid was changed to  4.91 g of 3-amino propane sulfonic acid and 10.45 g of  triphenylsulfonium bromide was changed to 12.65 g of the  following sulfonium salt.  Compound (Al 7) was obtained by performing salt  exchange between sodium taurocholate (produced by Tokyo  Chemical Industry Co., Ltd.) and the sulfonium salt (C).  $^{1}$H-NMR (400 MHz, d6-DMSO) 0.6 (s, 3H), 0.8 (s, 3H),  0.9 (d, 3H), 2.6 (dd, 2H), 3.2 (m, lH), 3.3 (dd, 2H), 3.6 (m,  lH), 3.8 (m, lH), 3.9 (s, !OH), 4.0 (bsd, lH), 4.3 (bsd, lH),  7.7 (m, 4H), 7.47 (t, 3H), 7.20-7.12 (m, 6H)  The compound (A18) was obtained with the same method  as in the synthesis of the compound (A3) except that  adamantane carbonyl chloride was changed to dehydro› cholic acid chloride.  The compound (A) used in the Examples and Compara› tive Examples is shown below.  <Compound (AlO)>  <Compound (All)>  <Compound (A12)>  <Compound (A13)>  <Compound (A14)>  <Compound (A15)>  <Compound (Al 7)>  <Compound (A18)>  <Compound (A16)> 