Hydrochloric Acid → (S)-2-((R)-2-(4-Fluoro-3-methylphenyl)-2-hydroxyethyl)pent-4-enoic acid
Reaction equation
[CH2:1]([C@H:4]1[CH2:8][C@H:7]([C:9]2[CH:14]=[CH:13][C:12]([F:15])=[C:11]([CH3:16])[CH:10]=2)[O:6][C:5]1=[O:17])[CH:2]=[CH2:3].[OH-:18].[K+].Cl>O1CCOCC1>[F:15][C:12]1[CH:13]=[CH:14][C:9]([C@H:7]([OH:6])[CH2:8][C@H:4]([CH2:1][CH:2]=[CH2:3])[C:5]([OH:17])=[O:18])=[CH:10][C:11]=1[CH3:16]Participants
5
Conditions
- Temperature
- 25 °C
Procedure
To a solution of 150 mg (3S,5R)-3-allyl-5-(4-fluoro-3-methylphenyl)dihydrofuran-2(3H)-one in 5 mL dioxane was added 5 mL aq. 5% KOH at 25° C. The mixture was stirred for 30 min at 25° C. then hydrolyzed with 10 mL of 1M HCl. The resulting mixture was extracted twice with ethyl acetate (10 mL). The combined organic layers were then extracted with 5 mL 5% K2CO3 three times and the combined aqueous layers acidified with 1M HCl to pH3. The resulting mixture was extracted with ethyl acetate (3×30 mL), the combined organic layers washed with brine (2×20 mL) before being concentrated under reduced pressure. The crude product residue was used for the next step without further purification.
Workup
- extractionThe resulting mixture was extracted twice with ethyl acetate (10 mL)
- extractionThe combined organic layers were then extracted with 5 mL 5% K2CO3 three times
- extractionThe resulting mixture was extracted with ethyl acetate (3×30 mL)
- washthe combined organic layers washed with brine (2×20 mL)
- concentrationbefore being concentrated under reduced pressure
- customThe crude product residue was used for the next step without further purification
Sources & evidence
- ORD record
- ord-01b023cdd8ff498c9d32a6f2643fe5d4
- Source dataset
- uspto-grants-2012_02
- Patent number
- US08119692B2
Reaction notes
Loading…