Water → HCID 23134214, compound

HRID 2220666Notes

Reaction equation

CS(O[CH2:6][CH2:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:20]=[CH:19][C:18]([C:21]([O:23][CH2:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)=[O:22])=[CH:17][CH:16]=2)=[CH:11][CH:10]=1)(=O)=O.[NH2:31][CH2:32][CH:33]([C:35]1[CH:36]=[CH:37][C:38]([OH:44])=[C:39]([NH:41][CH:42]=[O:43])[CH:40]=1)[OH:34].O.C(OCC)(=O)C>CN(C)C=O>[CH:42]([NH:41][C:39]1[CH:40]=[C:35]([CH:33]([OH:34])[CH2:32][NH:31][CH2:6][CH2:7][O:8][C:9]2[CH:10]=[CH:11][C:12]([C:15]3[CH:20]=[CH:19][C:18]([C:21]([O:23][CH2:24][C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)=[O:22])=[CH:17][CH:16]=3)=[CH:13][CH:14]=2)[CH:36]=[CH:37][C:38]=1[OH:44])=[O:43]

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of benzyl 4′-(2-methanesulfonyloxyethoxy)-biphenyl-4-carboxylate (0.117 g) and N-[5-(2-amino-1-hydroxyethyl)-2-hydroxyphenyl]formamide (0.054 g) in N,N-dimethylformamide (2 mL) was stirred at 80° C. overnight. Water and ethyl acetate were added to the reaction mixture. The organic layer was separated, washed with water and brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (eluent: methylene chloride/methanol=20/1-10/1) to afford benzyl 4′-{2-[2-(3-formylamino-4-hydroxyphenyl)-2-hydroxyethylamino]ethoxy}biphenyl-4-carboxylate (0.016 g).

Workup

customThe organic layer was separated
washwashed with water and brine
dry with materialdried over anhydrous magnesium sulfate
customThe solvent was evaporated under reduced pressure
customthe residue was purified by silica gel column chromatography (eluent: methylene chloride/methanol=20/1-10/1)

Sources & evidence

ORD record: ord-dd5846212fbb4c76aaaaff0cb672c1a0
Source dataset: uspto-grants-2008_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07417169B2

Reaction notes

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