Potassium Carbonate → {(R)-1-[4-(2-Ethyl-butoxy)-2-methoxy-phenyl]-2-hydroxy-ethyl}-carbamicacid tert-butyl ester

HRID 454969Notes

Reaction equation

[C:1]([O:5][C:6](=[O:20])[NH:7][C@H:8]([C:11]1[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][C:12]=1[O:18][CH3:19])[CH2:9][OH:10])([CH3:4])([CH3:3])[CH3:2].[CH2:21]([CH:23]([CH2:26][CH3:27])[CH2:24]Br)[CH3:22].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.CCOCC>[C:1]([O:5][C:6](=[O:20])[NH:7][C@H:8]([C:11]1[CH:16]=[CH:15][C:14]([O:17][CH2:24][CH:23]([CH2:26][CH3:27])[CH2:21][CH3:22])=[CH:13][C:12]=1[O:18][CH3:19])[CH2:9][OH:10])([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 60 °C

Procedure

To 34 mg (0.122 mmol) of the [(R)-2-hydroxy-1-(4-hydroxy-2-methoxy-phenyl)-ethyl]-carbamic acid tert-butyl ester and 2-ethylbutylbromide (20 ul, 0.182 mmol) dissolved in 1 ml DMF was added K2CO3 (34 mg, 0.244 mmol) and heated to 60° C. overnight. It was cooled to rt, diluted with ether, and quenched with water. The organic layer was washed with water and brine, and then dried over MgSO4. After removal of the solvent, the residue was purified by flash column (35% EtOAc in hexane) to give the titled compound (24 mg, 54%).

Workup

temperatureIt was cooled to rt
customquenched with water
washThe organic layer was washed with water and brine
dry with materialdried over MgSO4
customAfter removal of the solvent
customthe residue was purified by flash column (35% EtOAc in hexane)

Sources & evidence

ORD record: ord-f596f97c5b684853b73f5db5a4ac8f66
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08497271B2

Reaction notes

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