Dimethylformamide → 5-{4-[2-(5-Benzyloxymethyl-2-oxooxazolidin-3-yl)propoxy]benzyl}thiazolidine-2,4-dione
Reaction equation
[CH2:1]([O:8][CH2:9][CH:10]([OH:31])[CH2:11][NH:12][CH:13]([CH3:30])[CH2:14][O:15][C:16]1[CH:29]=[CH:28][C:19]([CH2:20][CH:21]2[S:25][C:24](=[O:26])[NH:23][C:22]2=[O:27])=[CH:18][CH:17]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CN(C)[CH:34]=[O:35]>>[CH2:1]([O:8][CH2:9][CH:10]1[O:31][C:34](=[O:35])[N:12]([CH:13]([CH3:30])[CH2:14][O:15][C:16]2[CH:29]=[CH:28][C:19]([CH2:20][CH:21]3[S:25][C:24](=[O:26])[NH:23][C:22]3=[O:27])=[CH:18][CH:17]=2)[CH2:11]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1Participants
Procedure
A procedure similar to that described in Example 4 was repeated, except that 200 mg of 5-{4-[2-(3-benzyloxy-2-hydroxypropylamino)propoxy]benzyl}thiazolidine-2,4-dione (prepared as described in Example 15), 73 mg of N,N'-carbonyldiimidazole and 20 ml of anhydrous dimethylformamide were used. The resulting crude product was purified by silica gel column chromatography, using a gradient elution method, with mixtures of ethyl acetate and hexane in ratios ranging from 2:1 to 3:1 by volume as the eluent, to give 160 mg of the title compound as a pale yellow glassy solid which was a mixture of a less polar diastereomer having an Rf value of 0.49 (on silica gel thin layer chromatography, using a 3:1 by volume mixture of ethyl acetate and hexane as the developing solvent) and a polar diastereomer having an Rf value of 0.38 (on silica gel thin layer chromatography, using a 3:1 by volume mixture of ethyl acetate and hexane as the developing solvent).
Workup
- customThe resulting crude product was purified by silica gel column chromatography
- washa gradient elution method
Sources & evidence
- ORD record
- ord-4a78a001bfda465b8bb7c353197be2eb
- Source dataset
- uspto-grants-1997_11
- Patent number
- US05688823
Reaction notes
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