Butylamine → Tert-butyl 2-(butylamino)acetate

To 36.5 g of butylamine was added with stirring 15.05 g of tert-butyl chloroacetate over a period of 30 minutes, while maintaining the temperature at 30°-70° C. The reaction mixture was held at 70° C for an additional 1 hour. At the end of this period, the excess butyl amine was evaporated in vacuo, and the residue was taken up in 40 ml of 2N NaOH solution and 50 ml of benzene, transferred into a separatory funnel and well shaken. The benzene solution was separated, washed with water, dried over anhydrous sodium sulfate and filtered. After evaporation of benzene, the residue was distilled under reduced pressure to give 17.0 g (90.9 percent) of N-butylglycine tert-butyl ester, B.P. 76° C/4 mmHg. The following amino acid tert-butyl esters not previously reported in the chemical literature were synthesized by the aforementioned procedure which is essentially that as taught by A. J. Speziale et al., J. Org. Chem. 25 731 (1960).

1. temperaturewhile maintaining the temperature at 30°-70° C
2. customAt the end of this period, the excess butyl amine was evaporated in vacuo
3. custom50 ml of benzene, transferred into a separatory funnel
4. customThe benzene solution was separated
5. washwashed with water
6. dry with materialdried over anhydrous sodium sulfate
7. filtrationfiltered
8. customAfter evaporation of benzene
9. distillationthe residue was distilled under reduced pressure

ORD record

ord-579f4a0dcf1844bd9711e4dcdb138f48

Source dataset

uspto-grants-1978_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04066773