RO5068760 → HCID 57935194, compound
Reaction equation
[OH:1][C@H:2]([CH2:38][OH:39])[CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([C@@H:11]2[C:15](=[O:16])[N:14]([C@@H:17]([C@H:29]([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[CH3:30])[C:18]([NH:20][C:21]3[CH:26]=[CH:25][C:24]([I:27])=[CH:23][C:22]=3[F:28])=[O:19])[C:13](=[O:37])[NH:12]2)=[CH:7][CH:6]=1>CO>[OH:1][C@H:2]([CH2:38][OH:39])[CH2:3][O:4][C:5]1[CH:6]=[CH:7][C:8]([C@H:11]2[C:15](=[O:16])[N:14]([C@@H:17]([C@H:29]([C:31]3[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=3)[CH3:30])[C:18]([NH:20][C:21]3[CH:26]=[CH:25][C:24]([I:27])=[CH:23][C:22]=3[F:28])=[O:19])[C:13](=[O:37])[NH:12]2)=[CH:9][CH:10]=1Participants
3
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Procedure
(2S,3S)-2-{(R)-4-[4-((R)-2,3-Dihydroxy-propoxy)-phenyl]-2,5-dioxo-imidazolidin-1-yl}-N-(2-fluoro-4-iodo-phenyl)-3-phenyl-butyramide (prepared as described in example 56) (160 mg, 0.25 mmol) was dissolved in methanol (10 ml) and allowed to stir for 48 hours at ambient temperature followed by warming to 50° C. for an additional 6 hours. The solvent was removed in vacuo and the residue was then purified by super-critical fluid chromatography using a Chiracel OD column eluted with carbon dioxide at 100 bar and 30° C. containing 35% methanol in acetonitrile eluted at 2 mL/minute. The second eluted compound was collected and concentrated in vacuo to obtain (2S,3S)-2-{(S)-4-[4-((R)-2,3-dihydroxy-propoxy)-phenyl]-2,5-dioxo-imidazolidin-1-yl}-N-(2-fluoro-4-iodo-phenyl)-3-phenyl-butyramide as a colorless solid (35 mg, 44%). The compound eluted first was identical with (2S,3S)-2-{(R)-4-[4-((R)-2,3-dihydroxy-propoxy)-phenyl]-2,5-dioxo-imidazolidin-1-yl}-N-(2-fluoro-4-iodo-phenyl)-3-phenyl-butyramide.