Reaction equation
C(OC([N:8]1[CH2:12][C@@H:11]([S:13][CH2:14][C:15]2[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=2)[CH2:10][C@H:9]1[C:23](=[O:25])[NH2:24])=O)(C)(C)C.O1CCOCC1.Cl.C(=O)(O)[O-].[Na+]>C(OCC)(=O)C>[C:23]([C@@H:9]1[CH2:10][C@H:11]([S:13][CH2:14][C:15]2[CH:16]=[CH:17][C:18]([O:21][CH3:22])=[CH:19][CH:20]=2)[CH2:12][NH:8]1)(=[O:25])[NH2:24]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
1.92 g of (2S, 4S)-1-(t-butoxycarbonyl)-2-carbamoyl-4-(4-methoxybenzylthio)pyrrolidine [prepared as described in step (4) above] was dissolved in 25 ml of ethyl acetate, and 26.2 ml of a 4N dioxane solution of hydrogen chloride were added to the solution, whilst ice-cooling. The mixture was then stirred at 0° to 5° C. for 2 hours and at room temperature for 30 minutes. At the end of this time, it was poured into a saturated aqueous solution of sodium bicarbonate, to make it weakly basic, and was extracted with ethyl acetate. The extract was washed with an aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate. The solvent was then removed by distillation under reduced pressure, to give 1.36 g of the title compound as a powder, melting at 120°-121° C.
Workup
- temperaturecooling
- extractionwas extracted with ethyl acetate
- washThe extract was washed with an aqueous solution of sodium chloride
- dry with materialdried over anhydrous magnesium sulfate
- customThe solvent was then removed by distillation under reduced pressure
Sources & evidence
- ORD record
- ord-5a57398a5c504dffb529c848afe88765
- Source dataset
- uspto-grants-1993_09
- Patent number
- US05242914
Linked notes
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