반응 #168157

반응 방정식

4-{(S)-1-[(S)-6-(2-hydroxy-2-methyl-propyl)-2-oxo-6-phenyl-[1,3]oxazin-an-3-yl]-ethyl}-benzoic acid hydrazide

toluene-4-sulfonic acid monohydrate

1,1,1-trimethoxy-ethane

→

title compound

(S)-6-(2-Methyl-allyl)-3-{(S)-1-[4-(5-methyl-[1,3,4]oxadiazol-2-yl)-phenyl]-ethyl}-6-phenyl-[1,3]oxazinan-2-one

용매

ethyl acetate

반응 조건

후처리

1. 1
   온도finally at reflux temperature for 1.5 h
2. 2
   온도After cooling to ambient temperature
3. 3
   세척the resulting mixture was washed with aqueous NaHCO3 solution and brine
4. 4
   기타The solvent was removed under reduced pressure
5. 5
   기타the residue was purified by chromatography on silica gel (CH2Cl2/MeOH 99:1→95:5)

실험 절차

A mixture of 4-{(S)-1-[(S)-6-(2-hydroxy-2-methyl-propyl)-2-oxo-6-phenyl-[1,3]oxazin-an-3-yl]-ethyl}-benzoic acid hydrazide (90 mg), toluene-4-sulfonic acid monohydrate (10 mg), and 1,1,1-trimethoxy-ethane (1 ml) was stirred at room temperature for 1 h, at 80° C. for 2 h, and finally at reflux temperature for 1.5 h. After cooling to ambient temperature, ethyl acetate was added and the resulting mixture was washed with aqueous NaHCO3 solution and brine. The solvent was removed under reduced pressure and the residue was purified by chromatography on silica gel (CH2Cl2/MeOH 99:1→95:5) to afford the title compound as a colorless resin-like solid.

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