Reaction equation
C[Si](C)(C(C)(C)C(C)C)[O:3][C:4]1[C:9]2[CH2:10][O:11][CH2:12][C@H:13]([C:21]3[O:25][N:24]=[C:23]([CH3:26])[N:22]=3)[NH:14][C:15](=[O:20])[CH2:16][S:17][C:18](=[O:19])[C:8]=2[C:7]([CH3:27])=[C:6]([O:28][CH3:29])[CH:5]=1.[F-].[NH4+]>CO.C(OCC)(=O)C>[OH:3][C:4]1[C:9]2[CH2:10][O:11][CH2:12][C@H:13]([C:21]3[O:25][N:24]=[C:23]([CH3:26])[N:22]=3)[NH:14][C:15](=[O:20])[CH2:16][S:17][C:18](=[O:19])[C:8]=2[C:7]([CH3:27])=[C:6]([O:28][CH3:29])[CH:5]=1Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Procedure
To a solution of 268 mg of (4R)-13-[dimethyl-(1,1,2-trimethylpropyl)-silanyloxy]-11-methoxy-10-methyl-4-(3-methyl-1,2,4-oxadiazol-5-yl)-3,4,5,6,7,9-hexahydro-1H-8,2,5-benzoxathiaazacycloundecine-6,9-dione in 10 ml of methanol were added 100 mg of ammonium fluoride, and the mixture was stirred for 30 min at room temperature. The mixture was diluted with 50 ml of ethyl acetate and washed with 30 ml of water and with 30 ml of brine. The organic layer was dried over sodium sulfate and the solvent was evaporated in vacuo. The residue was dissolved in ethyl acetate, then hexane was added, and the white solid was isolated by filtration to give 178 mg of (4R)-13-hydroxy-11-methoxy-10-methyl-4-(3-methyl-1,2,4-oxadiazol-5-yl)-3,4,5,6,7,9-hexahydro-1H-8,2,5-benzoxathiaazacycloundecine-6,9-dione as a white powder, m.p. 194°-196° C.
Workup
- washwashed with 30 ml of water and with 30 ml of brine
- dry with materialThe organic layer was dried over sodium sulfate
- customthe solvent was evaporated in vacuo
- dissolutionThe residue was dissolved in ethyl acetate
- additionhexane was added
- customthe white solid was isolated by filtration
Sources & evidence
- ORD record
- ord-c3631bb379754b42bc55f913bf574756
- Source dataset
- uspto-grants-1997_01
- Patent number
- US05594135
Linked notes
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