Water → (4S,5R)-3-t-butoxycarbonyl-2-(2,4-dimethoxyphenyl)-4-phenyl-5-methoxycarbonyl-1,3-oxazolidine

HRID 1683353

Reaktionsgleichung

Reaktionsgleichung von HRID 1683353
[C:1]([O:5][C:6]([NH:8][C@@H:9]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C@@H:10]([OH:15])[C:11]([O:13][CH3:14])=[O:12])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:22][O:23][C:24]1[CH:31]=[C:30]([O:32][CH3:33])[CH:29]=[CH:28][C:25]=1[CH:26]=O.O>C1(C)C=CC=CC=1>[C:1]([O:5][C:6]([N:8]1[C@@H:9]([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[C@H:10]([C:11]([O:13][CH3:14])=[O:12])[O:15][CH:26]1[C:25]1[CH:28]=[CH:29][C:30]([O:32][CH3:33])=[CH:31][C:24]=1[O:23][CH3:22])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Komponenten

5

Edukt 3

HCID 962WaterHCID 691752,4-DimethoxybenzaldehydeHCID 11140973Methyl (alphaR,betaS)-beta-(((1,1-dimethylethoxy)carbonyl)amino)-alpha-hydroxybenzenepropanoate

Produkt 1

HCID 53987440(4S,5R)-3-t-butoxycarbonyl-2-(2,4-dimethoxyphenyl)-4-phenyl-5-methoxycarbonyl-1,3-oxazolidineAusbeute 93,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
20 °C

Versuchsvorschrift

A solution of 0.497 g of methyl (2R,3S)-3-t-butoxycarbonylamino-2-hydroxy-3-phenylpropionate, 0.012 g of pyridinum b-toluenesulphonate and 0.295 g of 2,4-dimethoxybenzaldehyde in 20 cm3 of anhydrous toluene is heated to reflux for 24 hours. The water formed during the reaction is removed by means of a Dean and Stark apparatus. After cooling to a temperature in the region of 20° C., the solution is washed with 37% (w/w) aqueous sodium hydrogen sulphite solution and then with saturated aqueous sodium bicarbonate solution. After concentration of the organic phase under reduced pressure, 0.700 g of (4S,5R)-3-t-butoxycarbonyl-2-(2,4-dimethoxyphenyl)-4-phenyl-5-methoxycarbonyl-1,3-oxazolidine is obtained in an 80% yield in the form of a virtually equimolecular mixture of the diastereo-isomeric forms A and B, the characteristics of which are as follows:

Aufarbeitung

  1. temperatureto reflux for 24 hours
  2. customis removed by means of a Dean and Stark apparatus
  3. washthe solution is washed with 37% (w/w) aqueous sodium hydrogen sulphite solution

Quellen und Nachweise

ORD-Eintrag
ord-51baaab74cf84ab49e5cc3a71e94c07b
Quelldatensatz
uspto-grants-1997_06
Patentnummer
US05637723

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