Glycolic Acid → N-(hydroxyacetyl)alanine ethyl ester

One equivalent each of hydroxyacetic acid (10.0 g), dicyclohexylcarbodiimide, (L)-alanine ethyl ester hydrochloride and imidazole was stirred in 500 mL acetonitrile. The reaction mixture, initially at 0° C. was allowed to warm to room temperature overnight and then heated at 65° C. for 2 hours. After the addition of an equal volume of toluene, the reaction mixture was filtered and the solvent removed by rotovaping from the filtrate to give crude product. An aliquot of the crude product was chromatographed on silica gel to give N-(hydroxyacetyl)alanine ethyl ester (61% yield). 1H NMR (300 MHz, DMSO-d6 /TMS): δ1.19 (t , 3H, J=7.1 Hz), δ1.31 (d, 3H, J=7.2 Hz), δ3.83 (s, 2H), δ4.09 (d×q, 2H, J=1.2 and 7.1 Hz, irradiation in the methyl region eliminates the smaller coupling constant), δ4.32 (d×q, 1H, J=7.3 and 7.3), and δ 8.31 (br d, 1H, J=7.2 Hz). 13C NMR (75 MHz, CDCl3 /TMS): 13.59, 17.54, 47.31, 61.02, 61.48, and 172.17. [α]25D =-4.1°±0.4° (c=1.99, CHCl3). HRMS: calcd for C7H14NO4 (M+H)+, 176.0923; found, 176.0921.

1. custominitially at 0° C.
2. temperatureheated at 65° C. for 2 hours
3. filtrationthe reaction mixture was filtered
4. customthe solvent removed
5. customto give crude product
6. customAn aliquot of the crude product was chromatographed on silica gel

ORD-Eintrag

ord-e55116d5341c48e188246557bcef5a81

Quelldatensatz

uspto-grants-1995_11

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US05466801