4-Toluenesulfonyl chloride → HCID 10786336, Verbindung

HRID 1081195Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1081195
[OH:1][CH2:2][C@@H:3]1[CH2:7][O:6][C:5]([CH3:9])([CH3:8])[N:4]1[C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11].[C:17]1([CH3:27])[CH:22]=[CH:21][C:20]([S:23](Cl)(=[O:25])=[O:24])=[CH:19][CH:18]=1>N1C=CC=CC=1.C(OCC)(=O)C>[CH3:9][C:5]1([CH3:8])[N:4]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[C@H:3]([CH2:2][O:1][S:23]([C:20]2[CH:21]=[CH:22][C:17]([CH3:27])=[CH:18][CH:19]=2)(=[O:25])=[O:24])[CH2:7][O:6]1

Komponenten

5

Edukt 2

HCID 73974-Toluenesulfonyl chlorideHCID 11053464(R)-4-Hydroxymethyl-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

Produkt 1

HCID 10786336HCID 10786336, VerbindungAusbeute 84,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1049PyridineLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A solution of 10.7 g of t-butyl (R)-4-hydroxymethyl-2,2-dimethyl-3-oxazolidinecarboxylate (J. Org. Chem. 52, 1987, 2361-64) in 107 ml of pyridine is treated with 9.7 g of p-toluenesulphonyl chloride. The reaction mixture is stirred for 17 hours, then taken up in ethyl acetate and washed with water. After drying and evaporation the residue is purified over silica gel with hexane/ethyl acetate (3:1). There are obtained 15.1 g of t-butyl (S)-2,2-dimethyl-4-(p-tolylsulfonyloxymethyl)-3-oxazolidinecarboxylate.

Aufarbeitung

  1. washwashed with water
  2. customAfter drying
  3. customevaporation the residue
  4. customis purified over silica gel with hexane/ethyl acetate (3:1)

Quellen und Nachweise

ORD-Eintrag
ord-9a59b9c89e294327b49785330063ead6
Quelldatensatz
uspto-grants-1996_12
Patentnummer
US05583133

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