Acetic Acid → t-butyl (1S)-2-(1H-benzimidazol-1-yl)-1-[(3-methylphenoxy)methyl]ethylcarbamate

HRID 12418Notes

Reaction equation

[NH2:1][C:2]1[CH:27]=[CH:26][CH:25]=[CH:24][C:3]=1[NH:4][CH2:5][C@H:6]([NH:16][C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20])[CH2:7][O:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH3:15])[CH:10]=1.[C:28](O)(=O)C>C(OCC)(=O)C>[N:4]1([CH2:5][C@H:6]([NH:16][C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20])[CH2:7][O:8][C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([CH3:15])[CH:10]=2)[C:3]2[CH:24]=[CH:25][CH:26]=[CH:27][C:2]=2[N:1]=[CH:28]1

Participants

Conditions

Temperature: 60 °C

Procedure

To the compound (85 mg) obtained in Step 2 were added methyl orthformate (1 ml) and acetic acid (50 μl), and the mixture was stirred at 60° C. for 1 hr. The mixture was diluted with ethyl acetate, and washed with 1N sodium hydroxide. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was evaporated. The obtained crude product was purified by silica gel chromatography (ethyl acetate-hexane) to give the title compound (60 mg).

Workup

washwashed with 1N sodium hydroxide
dry with materialThe organic layer was dried over anhydrous magnesium sulfate
customthe solvent was evaporated
customThe obtained crude product
customwas purified by silica gel chromatography (ethyl acetate-hexane)

Sources & evidence

ORD record: ord-d2d1e0576b6c46f9ab8141cfe892bc38
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07728005B2

Reaction notes

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