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[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$_{3 }$ -) 

Synthesis of benzyltrimethylammonium 2-(24-nor- 5~-cholane-3, 7, 12-trion-23-ylcarbonyloxy)-1, 1,3,3, 3-pentafluoropropane-1-sulfonate (Additive-3) 

## [0145] 

<img src='content_image/905566.jpg'>

[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 

## Synthesis Example 1-3 

Additive-3 

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) 

## [0152] 

<img src='content_image/905565.jpg'>

[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- 

## Synthesis Example 1-4 

Additive-4 

