content_image/922117.jpg content_image/922122.jpg content_image/922123.jpg content_image/922119.jpg content_image/922121.jpg
<img src='content_image/922117.jpg'>

[1144] The obtained compound (III) was analyzed by NMR. 

[1145] $^{1}$H-NMR (DMSO-d6, 400 MHz): Ii (ppm)=4.74-4. 83 (t, 1H$_{2}$OH), 4.18-4.22 (t, 2H, Ha), 3.59-3.64 (q, 2H, H 6 ) 

[1146] $^{19}$F-NMR (DMSO-d6, 376 MHz): Ii (ppm)=-106.6 

[1147] From the results shown above, it was confirmed that the compound (III) had a structure shown below. 

<img src='content_image/922122.jpg'>

[1148] (ii) Synthesis of Compound (IV) 

[1149] To 1.00 g of the compound (III) and 3.00 g of aceto› nitrile were dropwise added 0.82 g of 1-adamantanecarbonyl chloride and 0.397 g oftriethylamine while cooling with ice. Then, the resultant was stirred at room temperature for 20 hours, followed by filtration. The filtrate was concentrated and dried, and dissolved in 30 g of dichloromethane, followed by washing with water three times. Thereafter, the organic phase was concentrated and dried, thereby obtaining 0.82 g of a compound (IV) (yield: 41 % ). 

<img src='content_image/922123.jpg'>

-continued 

[Chemical Formula 106] 

[Chemical Formula 107] 

<img src='content_image/922119.jpg'>

[1150] The obtained compound (IV) was analyzed by NMR. 

[1151] $^{1}$H-NMR (DMSO-d6, 400 MHz): Ii (ppm)=8.81 (s, lH, ff), 4.37-4.44 (t, 2H, Hd), 4.17-4.26 (t, 2H, ff), 3.03-3. 15 (q, 6H, H 6 ), 1.61-1.98 (m, 15H, Adamantane), 1.10-1.24 (t, 9H, Ha) 

[1152] $^{19}$F-NMR (DMSO-d6, 376 MHz): Ii (ppm)=-106. 61 

[1153] From the results above, it was confirmed that the compound (IV) had a structure shown below. 

<img src='content_image/922121.jpg'>

[1154] (iii) Synthesis of Compound (VI) 

[1155] 4 g of the compound (V) was dissolved in 79.8 g of dichloromethane. After confirming that the compound (VI) had dissolved in dichloromethane, 6.87 g of potassium car› bonate was added thereto, and 3.42 g of methyl adamantyl bromoacetate was further added. A reaction was effected under reflux for 24 hours, followed by filtration, washing with water, and crystallization with hexane. The resulting powder was dried under reduced pressure, thereby obtaining 3 .98 g of an objective compound (VI) (yield: 66%). 

[1156] The obtained compound (VI) was analyzed by NMR. 

[1157] $^{1}$H-NMR (CDC1$_{3}$ , 400 MHz): Ii (ppm)=7.83-7.86 (m, 4H, Phenyl), 7.69-7.78 (m, 6H, Phenyl), 7.51 (s, 2H, Hd), 4.46 (s, 2H, ff), 2.39 (s, 6H, Ha), 2.33 (s, 2H, Adamantane ), 2.17 (s, 2H,Adamantane), 1.71-1.98 (m, llH,Adamantane), 1.68 (s, 3H, H 6 ), 1.57-1.61 (m, 2H, Adamantane) 

[1158] From the results above, it was confirmed that the compound (VI) had a structure shown below. 

-continued 

[Chemical Formula 108] 

