Acetic Acid → (2S,3S)-2-amino-3-hydroxybutanedioic acid

Temperature

0 °C

(3S)-3-Hydroxyaspartic acid is prepared by the method of G. Cardillo, L. Gentilucci, A. Tolomelli, C. Tomasini, Synlett 1999, 1727-1730, and converted in analogy to P. G. Mattingly, M. J. Miller, J. Org. Chem. 1983, 48, 3556-3559, using microwave radiation in a closed reactor into (2S,3S)-2-amino-3-hydroxy-4-methoxy-4-oxobutyric acid hydrochloride. (2S,3S)-2-Amino-3-hydroxy-4-methoxy-4-oxobutyric acid hydrochloride (447 mg, 2.24 mmol) is dissolved in DMF (9 ml). The solution is cooled to 0° C., Boc-glycin-N-hydroxysuccinimide ester (763 mg, 2.91 mmol, 1.3 equivalents), DMAP (14 mg, 0.11 mmol, 0.05 equivalents) and finally DIPEA (1170 μl, 6.72 mmol, 3 equivalents) are added. The mixture is allowed to warm slowly to room temperature and is then stirred for 2 h. The mixture is acidified with glacial acetic acid, mixed with acetonitrile and chromatographed on Sephadex LH 20 (method 45). Product-containing fractions are combined, concentrated and again chromatographed (method 46). The obtained product (761 mg, quant.) is reacted further without further purification. For analytical purposes, a pure sample is obtained by HPLC (method 44).

1. temperatureto warm slowly to room temperature
2. customchromatographed on Sephadex LH 20 (method 45)
3. concentrationconcentrated
4. customagain chromatographed (method 46)
5. customThe obtained product (761 mg, quant.) is reacted further without further purification
6. customFor analytical purposes, a pure sample is obtained by HPLC (method 44)

ORD record

ord-24acce39a6d548de909c34db03e57584

Source dataset

uspto-grants-2011_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08076285B2