Ammonium Chloride → HCID 45082712, compound

To a solution of ethyl 2-(3-trimethylsilyl-N-methylprop-2-ynoylamino)acetate (5.28 g, 21.9 mmol) in THF (80 mL) was added dropwise a solution of TBAF (1M in THF, 24.0 mL, 24.0 mmol). After stirring for 10 min, a saturated NH4Cl solution (150 mL) was added and the resulting mixture was extracted with EtOAc (3×100 mL). The organic layer was washed with a saturated NaCl solution (400 mL), dried (Na2SO4) and concentrated under reduced pressure. The crude product was purified by flash chromatography (50% EtOAc/hex) to give ethyl 2-(N-methylprop-2-ynoylamino)acetate (1.9 g, 51%) as a yellow oil: TLC (50% EtOAc/hex) Rf 0.50; 1H NMR (CDCl3; a mixture of two rotomers) δ 1.26-1.33 (m, 3H), 3.03 (s, 1.2H), 3.29 (s, 1.8H), 3.09 (s, 0.43H), 3.17 (s, 0.57H), 4.16 (s, 1.1H), 4.33 (s, 0.9H), 4.17-4.28 (m, 2H).

1. extractionthe resulting mixture was extracted with EtOAc (3×100 mL)
2. washThe organic layer was washed with a saturated NaCl solution (400 mL)
3. dry with materialdried (Na2SO4)
4. concentrationconcentrated under reduced pressure
5. customThe crude product was purified by flash chromatography (50% EtOAc/hex)

ORD record

ord-d4fbe074c31e4d22b58b1775ae93bb37

Source dataset

uspto-grants-2004_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06784167B2