Water → HCID 23729347, compound

Reaction equation

[CH2:1]([O:3][C:4](=[O:37])[N:5]([CH2:22][C:23]1[CH:28]=[C:27]([C:29]([F:32])([F:31])[F:30])[CH:26]=[C:25]([C:33]([F:36])([F:35])[F:34])[CH:24]=1)[CH2:6][C:7]1[C:8]([S:18][CH2:19][CH2:20][CH3:21])=[N:9][C:10]2[C:15]([CH:16]=1)=[CH:14][CH:13]=[CH:12][C:11]=2[CH3:17])[CH3:2].[OH2:38]>CO.C(Cl)Cl>[CH2:1]([O:3][C:4](=[O:37])[N:5]([CH2:22][C:23]1[CH:24]=[C:25]([C:33]([F:36])([F:34])[F:35])[CH:26]=[C:27]([C:29]([F:30])([F:32])[F:31])[CH:28]=1)[CH2:6][C:7]1[C:8]([S:18]([CH2:19][CH2:20][CH3:21])=[O:38])=[N:9][C:10]2[C:15]([CH:16]=1)=[CH:14][CH:13]=[CH:12][C:11]=2[CH3:17])[CH3:2]

Participants

Procedure

(3,5-bis-trifluoromethyl-benzyl)-(8-methyl-2-propylsulfanyl-quinolin-3-ylmethyl)-carbamic acid ethyl ester (Example 135) (116 mg, 0.18 mmol) was dissolved in methanol (2 mL) and water (2 mL) followed by the addition of magnesium bis(mono peroxy phthalate hexahydrate) (MMPP) (267.1 mg, 0.54 mmol). The resulting mixture was stirred at room temperature overnight. The sample was diluted with methylene chloride and washed one time with water andone time with brine. The organic phase was dried, filtered and concentrated by rotary evaporation. The resulting sample was dried overnight under vacuum. (Biotage Horizon HPFC chromatography system, SiO2, 70:80 hexanes: ethyl acetate) gave a whit solid (80 mg, 72%).