[NH2:1][C@@:2]1([C:22]#[N:23])[C@H:7]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][C:13]([Cl:16])=[C:12]([Cl:17])[CH:11]=2)[CH2:6][C@@H:5]2[C@H:3]1[C@@:4]2([F:21])[C:18]([NH2:20])=[O:19].N[C@]1(C#N)[C@H](OCC2C=CC(Cl)=C(Cl)C=2)C[C@@H]2[C@H]1[C@@]2(F)C(N)=O.[C:47]1([CH3:57])[CH:52]=[CH:51][C:50]([S:53]([OH:56])(=[O:55])=[O:54])=[CH:49][CH:48]=1>C(OCC)(=O)C>[C:47]1([CH3:57])[CH:48]=[CH:49][C:50]([S:53]([OH:56])(=[O:54])=[O:55])=[CH:51][CH:52]=1.[NH2:1][C@@:2]1([C:22]#[N:23])[C@H:7]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][C:13]([Cl:16])=[C:12]([Cl:17])[CH:11]=2)[CH2:6][C@@H:5]2[C@H:3]1[C@@:4]2([F:21])[C:18]([NH2:20])=[O:19]To ethyl acetate (5 mL) solution containing 251.7 mg of the mixture of ((1R,2S,3R,5R,6R)-2-amino-2-cyano-3-[(3,4-dichloro benzyl)oxy]-6-fluoro bicyclo[3.1.0]hexane-6-carboxamide (6a) and (1R,2R,3R,5R,6R)-2-amino-2-cyano-3-[(3,4-dichloro benzyl)oxy]-6-fluoro bicyclo[3.1.0]hexane-6-carboxamide (8a) [containing (6a): 172.0 mg and (8a): 75.3 mg], 139.4 mg (content: 98 wt %) of p-toluene sulfonic acid was added and stirred for 18 hrs and 20 min at room temperature. The resulting slurry was filtered under suction, washed with 2 mL of ethyl acetate, and dried under reduced pressure at room temperature. 233.2 mg of the resulting colorless powder (248.0 mg obtained) was suspended in 2.5 mL of ethyl acetate, and stirred at room temperature for 15.5 hrs. The resulting slurry was filtered under suction, washed with 2 mL of ethyl acetate, and dried under reduced pressure at room temperature to obtain 220.6 mg of (1R,2S,3R,5R,6R)-2-amino-2-cyano-3-[(3,4-dichloro benzyl)oxy]-6-fluoro bicyclo[3.1.0]hexane-6-carboxamide p-toluene sulfonate (6e) as a colorless solid.
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