Methyl iodide → (2R)-2-[(methoxycarbonyl)amino]-3-methyl-3-(methylsulfanyl)butanoic Acid
Reaction equation
[NH2:1][C@H:2]([C:7]([OH:9])=[O:8])[C:3]([SH:6])([CH3:5])[CH3:4].[OH-].[Na+].[CH3:12]I.Cl[C:15]([O:17][CH3:18])=[O:16]>CO>[CH3:18][O:17][C:15]([NH:1][C@@H:2]([C:3]([CH3:5])([S:6][CH3:12])[CH3:4])[C:7]([OH:9])=[O:8])=[O:16]Participants
6
Conditions
- Temperature
- 0 °C
Procedure
A solution of L-penicillamine (0.5 g, 3.35 mmol) in methanol (3.3 mL) at 0° C. was treated with aqueous NaOH solution (3.7 mL, 1 N) and methyl iodide (0.23 mL, 3.69 mmol), stirred at 0° C. for 16 hours, treated with additional aqueous NaOH solution (3.5 mL, 3 N) at 0° C., followed by methyl chloroformate (0.5 mL, 6.47 mmol), warmed to 25° C. and stirred for 3 hours, and partitioned between ethyl acetate and water. The organic phase was washed with brine and dried over MgSO4, filtered and concentrated to give the title compound (0.428 g, 58% yield), which was used without further purification.
Workup
- temperaturewarmed to 25° C.
- stirringstirred for 3 hours
- custompartitioned between ethyl acetate and water
- washThe organic phase was washed with brine
- dry with materialdried over MgSO4
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-6448445d821a4d6eacaa26e8fc1cfd8a
- Source dataset
- uspto-grants-2010_11
- Patent number
- US07834043B2
Reaction notes
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