Dimethylformamide → 3-(2-t-Butyldimethylsilyloxy-1-methylethyl)-5-(4-methoxyphenoxymethyl)oxazolidin-2-one
Reaction equation
[CH3:1][O:2][C:3]1[CH:25]=[CH:24][C:6]([O:7][CH2:8][CH:9]([OH:23])[CH2:10][NH:11][CH:12]([CH3:22])[CH2:13][O:14][Si:15]([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:17])[CH3:16])=[CH:5][CH:4]=1.CN(C)[CH:28]=[O:29]>>[Si:15]([O:14][CH2:13][CH:12]([N:11]1[CH2:10][CH:9]([CH2:8][O:7][C:6]2[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:25][CH:24]=2)[O:23][C:28]1=[O:29])[CH3:22])([C:18]([CH3:19])([CH3:20])[CH3:21])([CH3:16])[CH3:17]Participants
3
Procedure
A procedure similar to that described in Preparation 11 was repeated, except that 3.36 g of 1-(4-methoxyphenoxymethyl)-2-(2-t-butyldimethylsilyloxy-1-methylethylamino)ethanol (prepared as described in Preparation 75), 1.78 g of N,N'-carbonyldiimidazole and 30 ml of anhydrous dimethylformamide were used, to give 1.42 g of the title compound having an Rf value of 0.41 (on silica gel thin layer chromatography, using a 1:2 by volume mixture of ethyl acetate and hexane as the developing solvent) from a polar diastereomer and 1.62 g of the title compound, melting at 81° C. to 85° C. from a less polar diastereomer.
Workup
- customA procedure similar to that described in Preparation 11
Sources & evidence
- ORD record
- ord-30ad2f00879e46998530e97d80cd31cb
- Source dataset
- uspto-grants-1997_11
- Patent number
- US05688823
Reaction notes
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