Oct. 21, 2010  59  US 2010/0266955 Al  acetone, and the precipitate was collected by filtration and  dried, thereby obtaining 184.5 g ofa compound (11) in the  form of a white solid (purity: 88.9%, yield: 95.5% ).  [Chemical Formula 66]  [0587]  The obtained compound (13) was analyzed by  NMR.  [0588]  $^{1}$H-NMR (DMSO-d6, 400 MHz):  Ii  (ppm)=4.74-4.  83 (t, lH, OH), 4.18-4.22 (t, 2H, Ha),3.59-3.64 (q, 2H, H 6 )  [0589]  $^{19}$F-NMR (DMSO-d6, 376 MHz):  Ii  (ppm)=-106.6  [0590]  From the results shown above, it was confirmed that  the compound (13) bad a structure shown below.  [0585]  Subsequently, 56.2 g of the compound (11) and  562.2 g of acetonitrile were prepared, and 77.4 g of p-tolu› enesulfonic acid monohydrate was added thereto. The result› ant was refluxed at 110°  C. for 3 hours. Then, the reaction  mixture was filtered, and the filtrate was concentrated and  dried to obtain a solid. 900 g oft-butyl methyl ether was added  to the obtained solid and stirred. Thereafter, the resultant was  filtered, and the residue was dried, thereby obtaining 22.2 g of  a compound (12) in the form of a white solid (purity: 91.0%,  yield: 44.9%).  [Chemical Formula 69]  [Chemical Formula 67]  [Chemical Formula 70]  [0586]  Subsequently, 4.34 g of the compound (12) (purity:  94.1 %), 3.14 g of 2-benzyloxyethanol and 43.4 g of toluene  were prepared, and 0.4 7 g of p-toluenesulfonic acid monohy› drate was added thereto. The resultant was refluxed at 105°  C.  for 20 hours. Then, the reaction mixture was filtered, and 20  g of hexane was added to the residue and stirred. Thereafter,  the resultant was filtered, and the residue was dried, thereby  obtaining 1.41 g ofa compound (13) (yield: 43.1%).  [0591]  Next, 1.00 g of the compound (13) and 3.00 g of  acetonitrile were prepared, and 0.82 g of 1-adamantanecar› bonyl chloride and 0.397 g of triethylamine were dropwise  added thereto while cooling with ice. Then, the resultant was  stirred at room temperature for 20 hours, followed by filtra› tion. 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 (14)  (yield: 41%).  [Chemical Formula 68]  NaOH  ----- 0  0  II  II  8 O-C-CF2-s-O 8  Na 0  II  0  (11)  0  0  II  II  8 o-C-CF 2 -s-o 0  II  0  (11)  p-TsOH-H2O  acetonitrile  0  0  II  II  HO-C-CF2-s-O 8  II  0  (12)  -continued  ~OH  0  +  #  (13)  --o-S03H-H20  (12)  (13) 