Reaction equation
S(Cl)([Cl:3])=O.[NH2:5][C:6]([CH3:11])([CH3:10])[C:7]([OH:9])=[O:8].[CH3:12]O>>[ClH:3].[NH2:5][C:6]([CH3:11])([CH3:10])[C:7]([O:9][CH3:12])=[O:8]Participants
Conditions
- Temperature
- 50 °C
Procedure
A 500 mL round bottomed flask equipped with nitrogen inlet, thermometer adapter, solids addition funnel, and magnetic stirrer was placed in an ice salt bath and charged with 100 mL of methanol. To this solution was added thionyl chloride(18.0 mL, 0.25 mol) via syringe at such a rate that the internal temperature was maintained at less than 0° C. This solution was then treated with aminoisobutyric acid (19.6g, 0.19 mol) portion wise from the addition funnel at such a rate that the temperature did not rise above 5° C. The ice bath was removed and replaced with an oil bath and the solution warmed to 50° C. for 1 h and then concentrated in vacuo. The salt was thoroughly dried under vacuum to give the desired product as a white solid 28 g, 96%, mp 185° C. 1H nmr (CDCl3) 300 MHz 8.87(brs, 3H), 3.74(s, 3H), 1.65(s, 6H).
Workup
- customA 500 mL round bottomed flask equipped with nitrogen inlet, thermometer adapter, solids addition funnel, and magnetic stirrer
- customwas placed in an ice salt bath
- temperaturewas maintained at less than 0° C
- customdid not rise above 5° C
- customThe ice bath was removed
- customreplaced with an oil bath
- concentrationconcentrated in vacuo
- customThe salt was thoroughly dried under vacuum
Sources & evidence
- ORD record
- ord-acac0781eb2d44a682d79a72323edaab
- Source dataset
- uspto-grants-1997_04
- Patent number
- US05622949
Linked notes
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