Potassium Carbonate → tert-butyl N-(4-cyanobenzyl)-N-methylglycinate

Temperature

60 °C

A mixture of alpha-bromo-p-tolunitrile (10.0 g, 51 mmol), sarcosine tert-butyl ester hydrochloride (10.2 g, 56 mmol) and potassium carbonate (21.2 g, 153 mmol) in acetone (100 mL) was stirred at 60° C. overnight. Resulting suspension was filtered off and salts were washed with acetone (2×150 mL). The filtrate was concentrated under reduced pressure. The residue was diluted with water (200 mL) and extracted with EtOAc (2×150 mL). The combined organic layers were washed with water (200 mL), dried (MgSO4) and the solvents were removed under reduced pressure to give the title compound as a yellow oil used without further purification (11.7 g, 88%). 1H NMR (DMSO-d6, 300 MHz) δ 7.79 (d, J=8.4 Hz, 2H), 7.51 (d, J=8.4 Hz, 2H), 3.71 (s, 2H), 3.20 (s, 2H), 2.23 (s, 3H), 1.42 (s, 9H). LC/MS (Method B): 260.9 (M+H)+.

1. customResulting suspension
2. filtrationwas filtered off
3. washsalts were washed with acetone (2×150 mL)
4. concentrationThe filtrate was concentrated under reduced pressure
5. additionThe residue was diluted with water (200 mL)
6. extractionextracted with EtOAc (2×150 mL)
7. washThe combined organic layers were washed with water (200 mL)
8. dry with materialdried (MgSO4)
9. customthe solvents were removed under reduced pressure

ORD record

ord-495fe27f977b45ccaa9e79492849daeb

Source dataset

uspto-grants-2014_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08802704B2