Hydrochloric Acid → HCID 68501061, compound

HRID 1176567Notes

Reaction equation

[CH2:1]([O:8][C:9]([CH:11]([O:33][CH:34]1[CH:39]([C:40]2[CH:45]=[CH:44][C:43]([O:46][CH2:47][CH2:48][CH2:49][O:50][CH2:51][C:52]3[CH:57]=[CH:56][CH:55]=[CH:54][C:53]=3[O:58][CH3:59])=[CH:42][CH:41]=2)[CH2:38][CH2:37][NH:36][CH2:35]1)[C:12]1[C:20]2[N:19]=[C:18]([C:21]([O:23][CH3:24])=[O:22])[N:17](COCC[Si](C)(C)C)[C:16]=2[CH:15]=[CH:14][CH:13]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.C(=O)([O-])O.[Na+]>CO>[CH2:1]([O:8][C:9]([CH:11]([O:33][CH:34]1[CH:39]([C:40]2[CH:41]=[CH:42][C:43]([O:46][CH2:47][CH2:48][CH2:49][O:50][CH2:51][C:52]3[CH:57]=[CH:56][CH:55]=[CH:54][C:53]=3[O:58][CH3:59])=[CH:44][CH:45]=2)[CH2:38][CH2:37][NH:36][CH2:35]1)[C:12]1[C:20]2[N:19]=[C:18]([C:21]([O:23][CH3:24])=[O:22])[NH:17][C:16]=2[CH:15]=[CH:14][CH:13]=1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 50 °C

Procedure

The mixture of 1.03 g of methyl 4-(1-benzyloxycarbonyl-4-{4-[3-(2-methoxybenzyloxy)propoxy]phenyl}piperidin-3-yloxymethyl)-1-(2-trimethylsilanylethoxymethyl)-1H-benzoimidazole-2-carboxylate, 10 ml of methanol and 10 ml of 2M HCl is stirred at 50° C. over 2 hours. The reaction mixture is cooled, poured onto aqueous 1M sodium hydrogencarbonate solution (70 ml) and extracted with tert-butyl methyl ether (2×100 ml). The organic phases are washed with brine, dried over sodium sulphate and concentrated by evaporation. The title compound is obtained as a white foam from the residue by means of flash chromatography (SiO2 60F). Rf=0.26 (2:1 EtOAc-heptane); Rt=5.11.

Workup

temperatureThe reaction mixture is cooled
extractionextracted with tert-butyl methyl ether (2×100 ml)
washThe organic phases are washed with brine
dry with materialdried over sodium sulphate
concentrationconcentrated by evaporation

Sources & evidence

ORD record: ord-c22152cc609a4a16bef8417f49b18656
Source dataset: uspto-grants-2010_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07842688B2

Reaction notes

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