Ethanol → N-hydroxy-2-[{[4'-(methoxymethyl)biphenyl-4-yl]carbonyl}(methyl)amino]-N'-methylpropanediamide
Reaction equation
C(O)C.[NH2:4][OH:5].[CH3:6][O:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:20]=[CH:19][C:18]([C:21](=[O:33])[N:22]([CH:24]([C:29]([NH:31][CH3:32])=[O:30])[C:25](OC)=[O:26])[CH3:23])=[CH:17][CH:16]=2)=[CH:11][CH:10]=1>O1CCCC1>[OH:5][NH:4][C:25](=[O:26])[CH:24]([N:22]([C:21]([C:18]1[CH:19]=[CH:20][C:15]([C:12]2[CH:11]=[CH:10][C:9]([CH2:8][O:7][CH3:6])=[CH:14][CH:13]=2)=[CH:16][CH:17]=1)=[O:33])[CH3:23])[C:29]([NH:31][CH3:32])=[O:30]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
Ethanol (5.0 mL) and a 50% aqueous solution (5.0 mL) of hydroxylamine were added to a tetrahydrofuran (5.0 mL) solution of 4-(methoxymethyl)-4′-{[1-methoxy-3-(methylamino)-1,3-dioxopropan-2-yl](methyl)carbamoyl}biphenyl (0.40 g) as obtained in Example 3-(4), and the mixture was stirred for 2 hours at room temperature. Then, the reaction mixture was concentrated under reduced pressure, and purified by preparative silica gel thin-layer chromatography (chloroform/methanol=85/15). IPE was added, and the precipitated solid was filtered off and dried to obtain N-hydroxy-2-[{[4′-(methoxymethyl)biphenyl-4-yl]carbonyl}(methyl)amino]-N′-methylpropanediamide (Compound 4, pink solid) (0.18 g, 46%).
Workup
- customas obtained in Example 3-(4)
- concentrationThen, the reaction mixture was concentrated under reduced pressure
- custompurified by preparative silica gel thin-layer chromatography (chloroform/methanol=85/15)
- additionIPE was added
- filtrationthe precipitated solid was filtered off
- customdried
Sources & evidence
- ORD record
- ord-a96a4c7e3f7f4f9cb4a795bcc037349a
- Source dataset
- uspto-grants-2015_07
- Patent number
- US09073821B2
Reaction notes
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