[C:1]([N:4]1[CH2:8][CH2:7][C:6]2([C:16]3[C:11](=[CH:12][CH:13]=[C:14]([S:17](Cl)(=O)=O)[CH:15]=3)[N:10]([C:21](=[O:26])[C:22]([F:25])([F:24])[F:23])[CH2:9]2)[CH2:5]1)(=[O:3])[CH3:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1.O>[C:1]([N:4]1[CH2:8][CH2:7][C:6]2([C:16]3[C:11](=[CH:12][CH:13]=[C:14]([SH:17])[CH:15]=3)[N:10]([C:21](=[O:26])[C:22]([F:24])([F:25])[F:23])[CH2:9]2)[CH2:5]1)(=[O:3])[CH3:2]The 1′-acetyl-1-(2,2,2-trifluoroacetyl)spiro[indoline-3,3′-pyrrolidine]-5-sulfonyl chloride (101 mg, 0.25 mmol) obtained as an intermediate in Step 2 of Example 236 was dissolved in tetrahydrofuran (3 mL). Thereafter, water (0.1 mL) and triphenylphosphine (0.23 g, 0.86 mmol) were added to the above obtained solution, and the thus obtained mixture was then stirred at 50° C. for 4 hours. Thereafter, the reaction solution was diluted with water, and was then extracted with ethyl acetate. The organic layer was washed with brine, and was then dried over anhydrous magnesium sulfate, followed by concentration in vacuo. The obtained residue was purified by preparative thin-layer chromatography (chloroform:methanol=20:1) to obtain 1-(1′-acetyl-5-mercaptospiro[indoline-3,3′-pyrrolidin]-1-yl)-2,2,2-trifluoroethanone (26 mg, 31%) in the form of a colorless oily product.
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