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

HRID 454969
Notes
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Reaction equation

HRID 454969 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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 77432Pentane, 3-(bromomethyl)-HCID 67073547[(R)-2-Hydroxy-1-(4-hydroxy-2-methoxy-phenyl)-ethyl]-carbamic acid tert-butyl ester

Product 1

HCID 67073758{(R)-1-[4-(2-Ethyl-butoxy)-2-methoxy-phenyl]-2-hydroxy-ethyl}-carbamicacid tert-butyl esterYield 54%

Reagents, catalysts & solvents 2

HCID 3283
Diethyl Ether
Solvent
HCID 6228DimethylformamideSolvent

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

  1. temperatureIt was cooled to rt
  2. customquenched with water
  3. washThe organic layer was washed with water and brine
  4. dry with materialdried over MgSO4
  5. customAfter removal of the solvent
  6. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes