Nov. 17,  2016  39  US 2016/0334706 Al  [0139]  In toluene solvent, 1-adamantanecarboxylic acid  was reacted with oxazolyl chloride to form a corresponding  carboxylic acid chloride, to which methylene chloride was  added to form a 25 wt % solution (corresponding to 0.4  mo!). Separately, another solution was prepared by mixing  151 g of Additive-I (in Synthesis Example 1-1 ), 45 g of  triethylamine, and 9 g of 4-dimethylaminopyridine in 750 g  of methylene chloride. Under ice cooling, the carboxylic  acid chloride/methylene chloride solution was added drop› wise to the other solution. After the completion of dropwise  addition, the solution was aged at room temperature for 10  hours. Thereafter, dilute hydrochloric acid was added to the  reaction solution to quench the reaction.  An  organic layer  was taken out, washed with water, and concentrated under  reduced pressure. Diisopropyl ether, 20 g, was added to the  concentrate for crystallization. The crystal was collected by  filtration and dried in vacuum, obtaining 193 g of the target  compound, benzyltrimethylammonium 2-(adamantane-l› carbony loxy )-1, 1,3 ,3 ,3-pentafluoropropane-1-sulfonate  (Additive-2), as white crystal (yield 80%).  [0140]  The target compound was analyzed by spectros› copy. The data of IR and TOFMS are shown below. The  NMR spectra, $^{1}$H- and $^{19}$F-NMR in DMSO-d$_{6 }$ are shown in  FIGS.  3  and  4.  On $^{1}$H-NMR analysis, water in DMSO-d$_{6 }$ was observed.  [0141]  IR (D-ATR): 2909, 2856, 1747, 1264, 1249, 1215,  1182, 1165, 1102, 108~ 992,917,888,839, 78~ 724,703,  640 cm- 1  [0142]  TOFMS (MALDI)  [0143]  Positive M+ 150 (corresponding to C$_{10}$H$_{16}$N+)  [0144]  Negative M- 391  (corresponding to CF$_{3}$CH  (OCOC$_{10}$H$_{15}$)CF$_{2}$SO$_{3 }$ -)  [0146]  While a mixture of3.8 g of Additive-I (in Synthe› sis Example 1-1), 4.2 g of dehydrocholic acid chloride, and  20 g of dichloromethane was ice cooled, a mixture of 1.0 g  oftriethylamine, 0.2 g of 4-dimethylaminopyridine and 5 g  [0153]  A solution was prepared by mixing 15 g of Addi› tive-3 (in Synthesis Example 1-3), 8.2 g of tetrabutylam› monium hydrogensulfate, 80 g of dichloromethane, and 40  g of water, and aged at room temperature for 30 minutes.  Thereafter, an organic layer was taken out, washed with  water, combined with methyl isobutyl ketone, and concen- of dichloromethane was added dropwise thereto. After the  completion of dropwise addition, the solution was aged at  room temperature for 10 hours. Dilute hydrochloric acid was  added to the reaction solution to quench the reaction.  An  organic layer was taken out, washed with water, combined  with methyl isobutyl ketone, and concentrated under  reduced pressure. Diisopropyl ether, 1,500 g, was added to  the concentrate for crystallization. The crystal was collected  by filtration and dried in vacuum, obtaining 6.1 g of the  target compound, benzyltrimethylammonium 2-(24-nor-53- cholane-3, 7, l 2-trion-23-ylcarbonyloxy )-1, 1,3,3,3-penta› fluoropropane- l-sulfonate (Additive-3), as white crystal  (yield 80%).  [0147]  The target compound was analyzed by spectros› copy. The data of IR and TOFMS are shown below. The  NMR spectra, $^{1}$H- and $^{19}$F-NMR in DMSO-d$_{6 }$ are shown in  FIGS.  5  and  6.  On $^{1}$H-NMR analysis, trace amounts of  residual solvents (diisopropyl ether and methyl isobutyl  ketone) and water in DMSO-d$_{6 }$ were observed.  [0148]  IR (D-ATR): 2968, 2876, 1768, 1706, 1491, 1478,  1459, 1380, 1245, 1218, 1184, 1169, 1120, 1073, 992, 921,  892, 727, 703, 643, 554 cm- 1  [0149]  TOFMS (MALDI)  [0150]  Positive M+ 150 (corresponding to C$_{10}$H$_{16}$N+)  [0151]  Negative M- 613  (corresponding to CF$_{3}$CH  (OCO-C$_{23}$H$_{33}$O$_{3}$)CF$_{2}$SO$_{3 }$-)  Synthesis of tetrabutylammonium 2-(24-nor-5~› cholane-3, 7, 12-trion-23-ylcarbonyloxy )-1, 1,3,3,3- pentafluoropropane-l-sulfonate (Additive-4)  Synthesis of benzyltrimethylammonium 2-(24-nor- 5~-cholane-3, 7, 12-trion-23-ylcarbonyloxy)-1, 1,3,3,  3-pentafluoropropane-1-sulfonate (Additive-3)  Additive-3  Additive-4  [0145]  Synthesis Example 1-3  Synthesis Example 1-4  [0152]  0  °’  -W- I  0  H 