Methylamine → HCID 19887910, compound

Temperature

0 °C

Methylamine (1.5 g, 23 mL of a 1 M THF solution, 48.38 mmol) solution was added dropwise to a −10° C. solution of ethyl chlorooxoacetate (5.0 g, 36.76 mmol) and triethylamine (5.6 g, 7.6 mL, 55.44 mmol) in dry THF (100 mL) under an argon atmosphere. After stirring at 0° C. for 1 h, then reaction was quenched with water (5 mL). Following another 20 min, the reaction mixture was extracted into ethyl acetate (2×30 mL) and the combined organic extracts were washed with water (2×100 mL), dried and concentrated in vacuo. The residue was purified by column chromatography using 40% EtOAc/hexanes to give monoethyl N-methyloxalamic acid (3.95 g, 82%) as a white powder. TLC: 75% EtOAc/hexane, Rf≈0.4; 1H NMR (CDCl3, 300 MHz) δ 4.35 (q, 2H, J=7.0 Hz), 2.92 (d, 3H, J=5.2 Hz), 1.37 (t, 3H, J=7.3 Hz).

1. customreaction
2. customwas quenched with water (5 mL)
3. waitFollowing another 20 min
4. extractionthe reaction mixture was extracted into ethyl acetate (2×30 mL)
5. washthe combined organic extracts were washed with water (2×100 mL)
6. customdried
7. concentrationconcentrated in vacuo
8. customThe residue was purified by column chromatography

ORD record

ord-9af7672532234ef58991dcada7fed6bf

Source dataset

uspto-grants-2016_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09272991B2