Methanol → HCID 43147868, compound
Reaction equation
O=S(Cl)Cl.[NH2:5][CH:6]([C:11]1[S:12][CH:13]=[CH:14][C:15]=1[CH3:16])[CH2:7][C:8]([OH:10])=[O:9].[CH3:17]O>>[NH2:5][CH:6]([C:11]1[S:12][CH:13]=[CH:14][C:15]=1[CH3:16])[CH2:7][C:8]([O:10][CH3:17])=[O:9]Participants
Procedure
To a 50 mL round bottom flask equipped with an electromagnetic stirrer and a drying tube, 15 mL of anhydrous methanol was added. The solution was cooled in an ice water-sodium chloride bath to minus 10° C., and 2 mL of SOCl2 was added slowly. The reaction mixture was allowed to react for an hour at room temperature. Then 1.85 g of 3-amino-3-(3-methyl-thiophene-2-yl)propionic acid was added. The mixture was allowed to react for 3 hours at room temperature, then refluxed for 40 minutes. After the solution was evaporated to remove the solvent, 100 mL of CHCl3 and 100 mL saturated NaHCO3 were added, and the layers were separated. The organic layer was washed successively with 30 mL of water and 30 mL of saturated brine, dried over anhydrous MgSO4, filtered, evaporated, and purified by column chromatography to give an oil-like product. MS (m/z): 200 [M+1]+.
Workup
- customTo a 50 mL round bottom flask equipped with an electromagnetic stirrer and a drying tube
- additionwas added slowly
- customto react for an hour at room temperature
- customto react for 3 hours at room temperature
- temperaturerefluxed for 40 minutes
- customAfter the solution was evaporated
- customto remove the solvent, 100 mL of CHCl3 and 100 mL saturated NaHCO3
- additionwere added
- customthe layers were separated
- washThe organic layer was washed successively with 30 mL of water and 30 mL of saturated brine
- dry with materialdried over anhydrous MgSO4
- filtrationfiltered
- customevaporated
- custompurified by column chromatography
- customto give an oil-like product
Sources & evidence
- ORD record
- ord-1f77988209dd461db17d03cc33b9644c
- Source dataset
- uspto-grants-2013_06
- Patent number
- US08466191B2
Reaction notes
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