Hydrochloric Acid → HCID 59728830, compound
Reaction equation
C[O:2][C:3](=[O:26])[CH2:4][CH2:5][C@@:6]1([CH3:25])[C:15](=[O:16])[CH2:14][CH2:13][CH:12]2[CH:7]1[CH2:8][CH2:9][C@:10]1([CH3:24])[C@@H:19]([C:20]([O:22][CH3:23])=[O:21])[CH2:18][CH2:17][CH:11]12.[CH3:27][N+](C)=C.[I-].CI.CCN(CC)CC.C1CCN2C(=NCCC2)CC1.Cl>ClCCl.O>[CH3:23][O:22][C:20]([C@@H:19]1[C@@:10]2([CH3:24])[CH2:9][CH2:8][CH:7]3[CH:12]([CH:11]2[CH2:17][CH2:18]1)[CH2:13][C:14](=[CH2:27])[C:15](=[O:16])[C@@:6]3([CH2:5][CH2:4][C:3]([OH:2])=[O:26])[CH3:25])=[O:21]Participants
Reactant 6
Product 1
Reagents, catalysts & solvents 2
Procedure
To a solution of 4-1 (24.5 g, 69.9 mmol) in 250 mL dichloromethane was added the Eschenmoser's salt (16.4 g, 174.8 mmol). The mixture was refluxed over 48 hr and then cooled to room temperature. After addition of MeI (8.7 mL, 139.8 mmol) and Et3N (24.4 mL, 174.8 mmol), the mixture was stirred at room temperature for 48 hr and concentrated. The residue was dissolved in dichloromethane (150 mL). DBU (21 mL, 139.8 mmol) was added. The mixture was stirred overnight and diluted with water (150 mL) and acidified with 6N HCl until pH=4. After removal of the solvent, the residue was extracted with EtOAc (×3). The combined organic layers was washed with brine and dried (MgSO4). Concentration of the mixture afforded a yellow solid as the desired product 4-2 which was further purified by recrystalization (methanol/water). MS calculated M-H2O: 344.5. Found 345.0
Workup
- temperatureThe mixture was refluxed over 48 hr
- concentrationconcentrated
- dissolutionThe residue was dissolved in dichloromethane (150 mL)
- stirringThe mixture was stirred overnight
- customAfter removal of the solvent
- extractionthe residue was extracted with EtOAc (×3)
- washThe combined organic layers was washed with brine
- dry with materialdried (MgSO4)
Sources & evidence
- ORD record
- ord-5e73b91d320343ec9261ff2eff7934e5
- Source dataset
- uspto-grants-2009_12
- Patent number
- US07625919B2
Reaction notes
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