Ethanol → 5-Fluoro-2-methyl-1-((4-(methylsulfinyl)phenyl)methylene)-1H-indene-3-acetic acid
Reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7](=[CH:11][C:12]1[CH:17]=[CH:16][C:15]([S:18]([CH3:20])=[O:19])=[CH:14][CH:13]=1)[C:6]([CH3:21])=[C:5]2[CH2:22]C(NCC(O)=O)=O.[CH2:30]([OH:32])C.[OH-:33].[Na+]>O>[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7](=[CH:11][C:12]1[CH:13]=[CH:14][C:15]([S:18]([CH3:20])=[O:19])=[CH:16][CH:17]=1)[C:6]([CH3:21])=[C:5]2[CH2:22][C:30]([OH:32])=[O:33]Participants
Procedure
N-[5-fluoro-2-methyl-1-(ρ-methylsulfinylbenzylidene)-3-indenylacetyl]-glycine. Benzyle-N-[5-fluoro-2-methyl-1-(ρ-methylsulfinylbenzylidene)-3-indenylacetyl]-glycinate (0.03 mole) in a mixture of 25 ml. of anhydrous ethanol and 2.5 ml. of 1N sodium hydroxide is allowed to stand at room temperature for 18 hours. The solution is diluted with water and extracted with ether. The aqueous layer is acidified with dilute hydrochloric acid and the organic product is extracted with ethyl acetate, washed with water and dried over sodium sulfate. Evaporation of the solution gives N-[5-fluoro-2-methyl-1-(ρ-methylsulfinylbenzylidene)-3-indenylacetic acid, the corresponding indenyl acyl glycine is obtained, which can be converted to the corresponding sulfonyl derivative using the procedure of Example 1E.
Workup
- extractionextracted with ether
- extractionthe organic product is extracted with ethyl acetate
- washwashed with water
- dry with materialdried over sodium sulfate
- customEvaporation of the solution
Sources & evidence
- ORD record
- ord-bef63433645e43c5a4e74076d54d0aa8
- Source dataset
- uspto-grants-1995_03
- Patent number
- US05401774
Reaction notes
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