Ethyl Acetate → HCID 15687402, compound
Reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[CH:4][C:3]=1[S:15][CH:16]([C:24]1[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][CH:25]=1)[CH:17]([OH:23])[C:18]([O:20]CC)=[O:19].[OH-].[K+].C(OCC)(=O)C.S([O-])(O)(=O)=O.[K+]>C(O)C.O>[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=2)=[CH:4][C:3]=1[S:15][CH:16]([C:24]1[CH:25]=[CH:26][C:27]([O:30][CH3:31])=[CH:28][CH:29]=1)[CH:17]([OH:23])[C:18]([OH:20])=[O:19]Participants
Procedure
3.28 g of ethyl 3-(2-amino-5-phenoxyphenyl)thio-2-hydroxy-3-(4-methoxyphenyl)propionate [prepared as described in step (a) above] were dissolved in 20 ml of ethanol, and a solution of 615 mg of 85% (by weight purity) caustic potash dissolved in 5 ml of water were added to the resulting solution. The solution was then stirred at room temperature for 2 hours, after which 50 ml of water and 70 ml of ethyl acetate Were added thereto, followed by an aqueous solution of potassium hydrogen sulfate sufficient to adjust the pH to a value of 3. The precipitate which formed was collected by filtration, to give 1.44 g of the title compound. The filtrate was separated, and the ethyl acetate layer was recovered, washed, dried over anhydrous magnesium sulfate, and concentrated by evaporation under reduced pressure. The residue was triturated in diethyl ether and then filtered to give a further 0.76 9 of the title compound. This substance was used in the subsequent step without purification.
Workup
- additionwere added to the resulting solution
- customThe precipitate which formed
- filtrationwas collected by filtration
Sources & evidence
- ORD record
- ord-7bd9404299e643ecaa0faeaba886faf4
- Source dataset
- uspto-grants-1991_03
- Patent number
- US05002942
Reaction notes
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