Potassium Carbonate → 3-[2-(3-Carboxy-1-propylthio)-4-methyl-1,3-thiazol-5-yl]-propionic acid
Reaction equation
[SH:1][C:2]1[S:3][C:4]([CH2:8][CH2:9][C:10]([O:12]CC)=[O:11])=[C:5]([CH3:7])[N:6]=1.C([O-])([O-])=O.[K+].[K+].Br[CH2:22][CH2:23][CH2:24][C:25]([O:27]CC)=[O:26].[OH-].[Na+]>C(O)C.CN(C=O)C>[C:25]([CH2:24][CH2:23][CH2:22][S:1][C:2]1[S:3][C:4]([CH2:8][CH2:9][C:10]([OH:12])=[O:11])=[C:5]([CH3:7])[N:6]=1)([OH:27])=[O:26]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 50 °C
Procedure
2 g (8.6 mmol) of ethyl 3-[2-mercapto-4-methyl-1,3-thiazol-5-yl]propionate were initially introduced into 40 ml of dry DMF, and 1.48 g (11 mmol) of powdered K2CO3 and 1.23 ml (8.6 mmol) of ethyl 4-bromobutyrate were added, and the reaction mixture was stirred at 50° C. for 2 hours. A solid residue was filtered off with suction, the DMF was removed in vacuo, and 3.6 g of a crude product were obtained, and this was taken up in 25 ml of ethanol. After addition of 1N sodium hydroxide solution, the mixture was stirred at room temperature for 2 hours, and the ethanol was removed in vacuo, and the aqueous residue was adjusted to pH 3 with hydrochloric acid. The solution was extracted with ethyl acetate, and the organic phase was dried with MgSO4 and evaporated. 2.2 g (88%) of the title compound were obtained as an oil.
Workup
- additionwere added
- filtrationA solid residue was filtered off with suction
- customthe DMF was removed in vacuo
- custom3.6 g of a crude product were obtained
- stirringthe mixture was stirred at room temperature for 2 hours
- customthe ethanol was removed in vacuo
- extractionThe solution was extracted with ethyl acetate
- dry with materialthe organic phase was dried with MgSO4
- customevaporated
Sources & evidence
- ORD record
- ord-188045fc3ec94a8fa6f37c7cf665f772
- Source dataset
- uspto-grants-1988_08
- Patent number
- US04762848
Reaction notes
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