Ammonia → HCID 57979876, compound

Temperature

-10 °C

N-[(benzyloxy)carbonyl]-O-isopropyl-L-serine (0.346 g, 1.23 mmol) was dissolved in tetrahydrofuran (5 ml) and the resulting solution was cooled to −10° C. N-methyl morpholine (0.189 g, 1.84 mmol) was added, followed by isobutylchloroformate (0.21 g, 1.48 mmol) over a period of 5 minutes. The reaction mixture was stirred for 10 minutes at −10° C. and aqueous ammonia (approximately 500 μl) was added in one portion and the reaction mixture was allowed to warm to room temperature. The resulting suspension was concentrated and extracted with EtOAc (2×20 ml). The combined extracts were washed with water (5 ml), 10% w/v aqueous solution of potassium hydrogensulfate, saturated aqueous sodium bicarbonate (5 ml) and water (5 ml). The organics were dried over magnesium sulfate filtered and concentrated to give benzyl [(1S)-2-amino-1-(isopropoxymethyl)-2-oxoethyl]carbamate as a white solid, (0.340 g, 100%); 1H NMR Spectrum: (CDCl3) 1.15 (m, 6H), 3.66 (m, 1H), 3.86 (m, 2H), 4.28 (m, 1H), 5.13 (s, 2H), 5.43 (br s, 1H), 5.72 (br s, 1H), 6.54 (br s, 1H), 7.35 (m, 5H).

1. temperatureto warm to room temperature
2. concentrationThe resulting suspension was concentrated
3. extractionextracted with EtOAc (2×20 ml)
4. washThe combined extracts were washed with water (5 ml), 10%
5. dry with materialThe organics were dried over magnesium sulfate
6. filtrationfiltered
7. concentrationconcentrated

ORD record

ord-afddfc2c60b84f529deacb7fe22e306e

Source dataset

uspto-grants-2009_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07632840B2