Diethyl Ether → 2-(4-(2-(Phenylmethyloxycarbonylamino)ethyl)phenoxy)-2-methylbutanoic Acid
Reaction equation
[C:1]1([CH2:7][O:8][C:9]([NH:11][CH2:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=2)=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(Cl)(Cl)Cl.[OH-:25].[Na+].[CH3:27][CH2:28]OCC.C[C:33](=[O:36])[CH2:34][CH3:35]>>[C:1]1([CH2:7][O:8][C:9]([NH:11][CH2:12][CH2:13][C:14]2[CH:15]=[CH:16][C:17]([O:20][C:34]([CH3:35])([CH2:27][CH3:28])[C:33]([OH:36])=[O:25])=[CH:18][CH:19]=2)=[O:10])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1Participants
6
Conditions
- Temperature
- 30 °C
Procedure
A solution of 4-(2-(phenylmethyloxycarbonylamino)ethyl)phenol (5.74 g; 21.16 mmole) in 2-butanone (17 mL) and chloroform (6 g) was added dropwise to a mixture of sodium hydroxide (9.0 g; 225 mmole) and 2-butanone (67 mL) whilst keeping the reaction temperature below 30° C. The mixture was allowed to stir at 30° C. for 4 h. Ether (100 mL) was added and the resultant solid was collected by filtration and washed with ether (100 mL). The solid was dissolved in water (70 mL) and any residual ether removed by evaporation. 1N Hydrochloric acid was added to adjust the pH to 1, and the resulting oil was extracted with dichloromethane (3×50 mL). The combined extracts were dried (Na2SO4) and evaporated to afford a yellow oil (3.82 g; 49%).
Workup
- customthe reaction temperature below 30° C
- filtrationthe resultant solid was collected by filtration
- washwashed with ether (100 mL)
- dissolutionThe solid was dissolved in water (70 mL)
- customany residual ether removed by evaporation
- addition1N Hydrochloric acid was added
- extractionthe resulting oil was extracted with dichloromethane (3×50 mL)
- dry with materialThe combined extracts were dried (Na2SO4)
- customevaporated
- customto afford a yellow oil (3.82 g; 49%)
Sources & evidence
- ORD record
- ord-3bfcf676f4b64c148044f07c3983f654
- Source dataset
- uspto-grants-2001_10
- Patent number
- US06306854B1
Reaction notes
Loading…