Dimethylformamide → 5-{4-[2-(5-Phenylthiomethyl-2-oxooxazolidin-3-yl)propoxy]benzyl}thiazolidine-2,4-dione
Reaction equation
[C:1]1([S:7][CH2:8][CH:9]([OH:30])[CH2:10][NH:11][CH:12]([CH3:29])[CH2:13][O:14][C:15]2[CH:28]=[CH:27][C:18]([CH2:19][CH:20]3[S:24][C:23](=[O:25])[NH:22][C:21]3=[O:26])=[CH:17][CH:16]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CN(C)[CH:33]=[O:34]>>[C:1]1([S:7][CH2:8][CH:9]2[O:30][C:33](=[O:34])[N:11]([CH:12]([CH3:29])[CH2:13][O:14][C:15]3[CH:28]=[CH:27][C:18]([CH2:19][CH:20]4[S:24][C:23](=[O:25])[NH:22][C:21]4=[O:26])=[CH:17][CH:16]=3)[CH2:10]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1Participants
3
Procedure
A procedure similar to that described in Example 4 was repeated, except that 1.2 g of 5-{4-[2-(3-phenylthio-2-hydroxypropylamino)propoxy]benzyl}thiazolidine-2,4-dione (prepared as described in Example 37), 0.52 g of N,N'-carbonyldiimidazole and 20 ml of anhydrous dimethylformamide were used, to give 1.15 g of the title compound as a 1:1 mixture of two kinds of diastereomers having an Rf value of 0.30 (polar) and an Rf value of 0.38 (less polar) (on silica gel thin layer chromatography, using a 1:1 by volume mixture of ethyl acetate and hexane as the developing solvent).
Sources & evidence
- ORD record
- ord-1b40918b7e224a16be6dc07f009b7487
- Source dataset
- uspto-grants-1997_11
- Patent number
- US05688823
Reaction notes
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