Tetrahydrofuran → HCID 69457443, compound

HRID 916084Notes

Reaction equation

[H-].[Na+].O1CCCC1.[CH3:8][O:9][C:10](=[O:28])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[CH2:17][S:18][C:19]1[NH:20][C:21]2[CH:27]=[CH:26][CH:25]=[CH:24][C:22]=2[N:23]=1.[C:29]([O:33][C:34](=[O:43])[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=1[CH2:41]Br)([CH3:32])([CH3:31])[CH3:30]>O>[CH3:8][O:9][C:10](=[O:28])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[CH2:17][S:18][C:19]1[N:20]([CH2:41][C:36]2[CH:37]=[CH:38][CH:39]=[CH:40][C:35]=2[C:34]([O:33][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:43])[C:21]2[CH:27]=[CH:26][CH:25]=[CH:24][C:22]=2[N:23]=1

Participants

Conditions

Temperature: 60 °C

Procedure

Sodium hydride (104 mg, 2.86 mmol) and tetrahydrofuran (16 ml) were added to a previously dried reaction vessel. To the mixture were added 2-(benzimidazole-2-ylthiomethyl)benzoic acid methyl ester (428 mg, 1.43 mmol) and 2-(bromomethyl)benzoic acid t-butyl ester (466 mg, 3.46 mmol), and then the mixture was stirred at 60° C. for 50 minutes. Water was added thereto, followed by extraction with ethyl acetate. After the ethyl acetate phase was dried with anhydrous sodium sulfate, it was concentrated, and the residue was purified by silica gel column chromatography (hexane: ethyl acetate=3:1) to obtain 2-((1-((2-((t-butyl)oxycarbonyl)phenyl)methyl)benzimidazole-2-ylthio)methyl)benzoic acid methyl ester (495 mg, yield 71%).

Workup

extractionfollowed by extraction with ethyl acetate
dry with materialAfter the ethyl acetate phase was dried with anhydrous sodium sulfate, it
concentrationwas concentrated
customthe residue was purified by silica gel column chromatography (hexane: ethyl acetate=3:1)

Sources & evidence

ORD record: ord-7a50594bf5f04aee9226b1bb558c5956
Source dataset: uspto-grants-2007_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07268145B2

Reaction notes

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