Water → (2R)-N-methyl-2-methylamino-3-(thiophen-2-yl)propionamide
Reaction equation
C(O[C:6](=O)[N:7](C)[C@@H:8]([C:15](=[O:18])[NH:16][CH3:17])[CH2:9][C:10]1[S:11][CH:12]=[CH:13][CH:14]=1)(C)(C)C.FC(F)(F)C(O)=O.O.C(=O)([O-])O.[Na+]>C(Cl)Cl>[CH3:17][NH:16][C:15](=[O:18])[C@H:8]([NH:7][CH3:6])[CH2:9][C:10]1[S:11][CH:12]=[CH:13][CH:14]=1Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
N-Methyl-N-((1R)-1-(methylcarbamoyl)-2-(thiophen-2-yl)ethyl)carbamic acid tert-butylester (1.17 g; 3.92 mmol) was dissolved in methylene chloride (4 ml). The reaction was cooled to 0° C. and triflouroacetic acid was added. The mixture was stirred at room temperature for 1.5 hour. Water (30 ml) and solid sodium hydrogencarbonate were added to pH 8. The phases were separated. The aqueous phase was extracted with methylene chloride (4×20 ml). The combined organic phases were dried over magnesium sulfate and the solvent was removed over vacuo to afford 0.70 g of (2R)-N-methyl-2-methylamino-3-(thiophen-2-yl)propionamide.
Workup
- customThe phases were separated
- extractionThe aqueous phase was extracted with methylene chloride (4×20 ml)
- dry with materialThe combined organic phases were dried over magnesium sulfate
- customthe solvent was removed over vacuo
Sources & evidence
- ORD record
- ord-585a53a6517d43fb866f437e3a05261e
- Source dataset
- uspto-grants-2005_09
- Patent number
- US06939880B2
Reaction notes
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