Citric Acid → HCID 59909741, compound
Reaction equation
CC(C)(C)C[C:4](=[O:20])[CH2:5][C@H:6]([C:10]1[O:11][CH:12]=[C:13]([C:15]([O:17]CC)=[O:16])[N:14]=1)[CH2:7][CH:8]=[CH2:9].O.[OH-].[Li+].[OH-].[Li+].C(O)(=O)[CH2:29][C:30]([CH2:35]C(O)=O)([C:32](O)=O)[OH:31]>O1CCOCC1.O>[C:30]([O:31][C:4](=[O:20])[CH2:5][C@H:6]([C:10]1[O:11][CH:12]=[C:13]([C:15]([OH:17])=[O:16])[N:14]=1)[CH2:7][CH:8]=[CH2:9])([CH3:35])([CH3:32])[CH3:29]Participants
Conditions
- Temperature
- 0 °C
Procedure
Two identical reactions were put on each containing the following: A solution of ethyl 2-[(1R)-1-(4,4-dimethyl-2-oxopentyl)-3-butenyl]-1,3-oxazole-4-carboxylate (Preparation 115) (4.0 g, 12.9 mmol) in 1,4-dioxan (40 ml) and water (20 ml) was cooled to 0° C. and treated with lithium hydroxide monohydrate (0.8 g, 19.0 mmol). The mixture was stirred at 0° C. for 4 hours. Further lithium hydroxide monhydrate (0.8 g, 19.0 mmol) was added and stirred at 0° C. for 10 minutes. The two reactions were combined and partitioned between ethyl acetate and water. The aqueous layer was neutralised with citric acid (16.3 g, 38.0 mmol) and extracted with ethyl acetate (×3). The combined organic extracts were washed with water and brine, dried over anhydrous sodium sulphate, filtered and the solvent removed under reduced pressure to afford the title compound as a colourless oil (8.3 g).
Workup
- stirringstirred at 0° C. for 10 minutes
- custompartitioned between ethyl acetate and water
- extractionextracted with ethyl acetate (×3)
- washThe combined organic extracts were washed with water and brine
- dry with materialdried over anhydrous sodium sulphate
- filtrationfiltered
- customthe solvent removed under reduced pressure
Sources & evidence
- ORD record
- ord-8ce416c360ae408286a9f04adfa48e7a
- Source dataset
- uspto-grants-2005_05
- Patent number
- US06897306B2
Reaction notes
Loading…