Diethyl Ether → N-p-methoxybenzyloxycarbonyl-D-serine benzyl ester

N-p-Methoxybenzyloxycarbonyl-D-serine (5.39 mg, 2.00 sm:ol; prepared as a colourless solid of m.p. 96°-97° C. in 60% yield by the dissolved in methanol and treated with a solution of potassium carbonate (138 mg, 1.00 mmol) in water (2 ml). The mixture is evaporated by dryness, N,N-dimethyl-forimide (DMF) is added and re-evaporated (2×2 ml), and the solid residue is then dissolved in dry warm DMF, benzyl bromide (248 μl, 2.1 mmol) is added and the solution is warmed in a dry closed flask at 50° C. for 1 hour. The resulting mixture is portioned between ether (10 ml) and water (10 ml) and the aqueous layer is extracted with ether (2×10 ml). The combined ether extracts are washed with saturated sodium bicarbonate (5 ml) and saturated brine (5 ml), dried and evaporated to dryness. The residue is purified on a column of silica gel using 1:1 v/v ethyl acetate:petroleum ether as eluant to yield to title compound as a homogenous oil (590 mg, 82%) which crystallises on standing to give a colourless solid of m.p. 67°-68° C. (from diethyl ether); [α]D20 --6.3° (c 4.0, CHCl3).

1. customprepared as a colourless solid of m.p. 96°-97° C. in 60% yield by the
2. customThe mixture is evaporated by dryness, N,N-dimethyl-forimide (DMF)
3. additionis added
4. customre-evaporated (2×2 ml)
5. dissolutionthe solid residue is then dissolved
6. customin dry
7. additionis added
8. temperaturethe solution is warmed in a dry
9. customclosed flask at 50° C. for 1 hour
10. extractionthe aqueous layer is extracted with ether (2×10 ml)
11. washThe combined ether extracts are washed with saturated sodium bicarbonate (5 ml) and saturated brine (5 ml)
12. customdried
13. customevaporated to dryness
14. customThe residue is purified on a column of silica gel using 1:1 v/v ethyl acetate

ORD-Eintrag

ord-0564436e5f8b4faab440d6d3b2019a4b

Quelldatensatz

uspto-grants-1991_02

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US04996313