1H-Benzo[d]imidazole-2-sulfonyl chloride → benzyl 4-(3-[(2S)-1-(1H-benzo[d]imidazol-2-ylsulfonyl)-2-piperidyl]-1,2,4-oxadiazol-5-ylmethoxy)-1-piperidinecarboxylate
Reaction equation
[NH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][C@H:2]1[C:7]1[N:11]=[C:10]([CH2:12][O:13][CH:14]2[CH2:19][CH2:18][N:17]([C:20]([O:22][CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)=[O:21])[CH2:16][CH2:15]2)[O:9][N:8]=1.[NH:30]1[C:34]2[CH:35]=[CH:36][CH:37]=[CH:38][C:33]=2[N:32]=[C:31]1[S:39](Cl)(=[O:41])=[O:40]>>[NH:30]1[C:34]2[CH:35]=[CH:36][CH:37]=[CH:38][C:33]=2[N:32]=[C:31]1[S:39]([N:1]1[CH2:6][CH2:5][CH2:4][CH2:3][C@H:2]1[C:7]1[N:11]=[C:10]([CH2:12][O:13][CH:14]2[CH2:15][CH2:16][N:17]([C:20]([O:22][CH2:23][C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=3)=[O:21])[CH2:18][CH2:19]2)[O:9][N:8]=1)(=[O:40])=[O:41]Participants
3
Reactant 2
Product 1
Procedure
The title compound was prepared by a similar method to Example 1 from benzyl 4-(3-[(2S)-2-piperidyl]-1,2,4-oxadiazol-5-ylmethoxy)-1-piperidinecarboxylate [see Preparation 95] and 1H-benzo[d]imidazol-2-sulfonyl chloride [see Preparation 8]. The crude product was purified by column chromatography on silica gel eluting with a solvent gradient of 80:20 changing to 0:100, by volume, hexane:ethyl acetate, in 5% increments, to afford benzyl 4-(3-[(2S)-1-(1H-benzo[d]imidazol-2-ylsulfonyl)-2-piperidyl]-1,2,4-oxadiazol-5-ylmethoxy)-1-piperidinecarboxylate as a clear oil.
Workup
- customThe crude product was purified by column chromatography on silica gel eluting with a solvent gradient of 80:20 changing to 0:100, by volume, hexane
Sources & evidence
- ORD record
- ord-b7bb11bd50bb4fb194fdbb7b991f20bf
- Source dataset
- uspto-grants-2003_08
- Patent number
- US06610707B1
Reaction notes
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