Diethyl Ether → HCID 102376807, compound
Reaction equation
[CH3:1][CH2:2][C@H:3]1[O:18][C:16](=[O:17])[C@H:15]([CH3:19])[C@@H:14]([O:20][C@@H:21]2[O:26][C@@H:25]([CH3:27])[C@H:24]([OH:28])[C@@:23]([O:30][CH3:31])([CH3:29])[CH2:22]2)[C@H:13]([CH3:32])[C@@H:12]([O:33][C@@H:34]2[O:39][C@H:38]([CH3:40])[CH2:37][C@H:36]([N:41]([CH3:43])[CH3:42])[C@H:35]2[OH:44])[C@@:11]([O:46][CH3:47])([CH3:45])[CH2:10][C@@H:9]([CH3:48])[C:7](=[O:8])[C@H:6]([CH3:49])[C@@H:5]([OH:50])[C@@:4]1([OH:52])[CH3:51].Cl[Sn]Cl.[N+](=[CH2:58])=[N-].C(OCC)C>CN(C=O)C.C([O-])(O)=O.[Na+]>[CH3:1][CH2:2][C@H:3]1[O:18][C:16](=[O:17])[C@H:15]([CH3:19])[C@@H:14]([O:20][C@@H:21]2[O:26][C@@H:25]([CH3:27])[C@H:24]([OH:28])[C@@:23]([O:30][CH3:31])([CH3:29])[CH2:22]2)[C@H:13]([CH3:32])[C@@H:12]([O:33][C@@H:34]2[O:39][C@H:38]([CH3:40])[CH2:37][C@H:36]([N:41]([CH3:42])[CH3:43])[C@H:35]2[OH:44])[C@@:11]([O:46][CH3:47])([CH3:45])[CH2:10][C@@H:9]([CH3:48])[C:7](=[O:8])[C@H:6]([CH3:49])[C@@H:5]([O:50][CH3:58])[C@:4]1([OH:52])[CH3:51]Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
Clarithromycin (J. Antibiot. 43 (1990) 544-549) (1.00 g, 1.34 mmol) and SnCl2 2H2O (0.307 g, 1.36 mmol) were dissolved in DMF (10 mL) and stirred at RT for 1 hour. A solution of diazomethane in diethylether prepared by Method B (cca 6 mmol) was added and the resulting mixture was stirred at RT for 4 hours. The mixture was diluted with aq. NaHCO3 (50 mL) and extracted with ethyl-acetate (3×30 mL). The organic layer was dried over Na2SO4, and concentrated to afford a mixture of the title and starting compounds (24%:73% LC-MS).
Workup
- stirringthe resulting mixture was stirred at RT for 4 hours
- extractionextracted with ethyl-acetate (3×30 mL)
- dry with materialThe organic layer was dried over Na2SO4
- concentrationconcentrated
- customto afford
- additiona mixture of the title
Sources & evidence
- ORD record
- ord-d3ef5dc0319d4f3494c7bdefa952216b
- Source dataset
- uspto-grants-2008_10
- Patent number
- US07435805B2
Reaction notes
Loading…