Water → ethyl (4'-(2-[(1S,2R)-2-hydroxy-2-(4-hydroxyphenyl)-1-methylethylamino]ethoxy}-2',6'-dimethylbiphenyl-4-yloxy)acetate

HRID 2243547Notes

Reaction equation

CS(O[CH2:6][CH2:7][O:8][C:9]1[CH:14]=[C:13]([CH3:15])[C:12]([C:16]2[CH:21]=[CH:20][C:19]([O:22][CH2:23][C:24]([O-:26])=[O:25])=[CH:18][CH:17]=2)=[C:11]([CH3:27])[CH:10]=1)(=O)=O.[NH2:28][C@@H:29]([CH3:39])[C@@H:30]([C:32]1[CH:37]=[CH:36][C:35]([OH:38])=[CH:34][CH:33]=1)[OH:31].O.[C:41](OCC)(=O)[CH3:42]>CN(C)C=O>[OH:31][C@H:30]([C:32]1[CH:37]=[CH:36][C:35]([OH:38])=[CH:34][CH:33]=1)[C@@H:29]([NH:28][CH2:6][CH2:7][O:8][C:9]1[CH:14]=[C:13]([CH3:15])[C:12]([C:16]2[CH:21]=[CH:20][C:19]([O:22][CH2:23][C:24]([O:26][CH2:41][CH3:42])=[O:25])=[CH:18][CH:17]=2)=[C:11]([CH3:27])[CH:10]=1)[CH3:39]

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of [4′-(2-methanesulfonyloxyethoxy)-2′,6′-di -methylbiphenyl-4-yloxy]acetate and 4-((1R,2S)-2-amino-1-hydroxypropyl)phenol (0.71 g) in N,N-dimethylformamide (10 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 an hydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (eluent: methylene chloride/methanol=10/1) to afford ethyl (4′-{2-[(1S,2R)-2-hydroxy-2-(4-hydroxyphenyl)-1-methyl-ethylamino]ethoxy}-2′,6′-dimethylbiphenyl-4-yloxy)acetate (0.47 g).

Workup

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

Sources & evidence

ORD record: ord-4044d8a781a94800a7b7c7c4d433926f
Source dataset: uspto-grants-2010_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07674938B2

Reaction notes

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