Ammonium Chloride → HCID 67246124, compound
Reaction equation
[F:1][C:2]([F:35])([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[CH2:3][O:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][N:11]1[CH2:15][C@@H:14]([C:16]2[CH:27]=[CH:26][C:19]3[O:20][C:21]([CH3:25])([CH3:24])[O:22][CH2:23][C:18]=3[CH:17]=2)[O:13]C1=O.C[Si](C)(C)[O-].[K+].[Cl-].[NH4+]>O1CCCC1>[F:35][C:2]([F:1])([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[CH2:3][O:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][NH:11][CH2:15][C@@H:14]([C:16]1[CH:27]=[CH:26][C:19]2[O:20][C:21]([CH3:25])([CH3:24])[O:22][CH2:23][C:18]=2[CH:17]=1)[OH:13]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 70 °C
Procedure
To a solution of Intermediate 35 (1.5 g, 3.0 mmol) in tetrahydrofuran (60 mL) was added potassium trimethylsilanolate (1.54 g, 12 mmol). The mixture was stirred at 70° C. under inert atmosphere for 2 hours. To the cooled reaction mixture was added saturated solution of ammonium chloride (60 mL). The suspension was extracted with methylene chloride (2×30 mL). The organic layer was washed with water (2×25 mL) and brine (25 mL), dried (Na2SO4) and the solvent removed under reduced pressure. The residue was purified by column chromatography with silica gel and methylene chloride/ethanol/ammonium hydroxide (100:8:1) as eluent. The title compound was obtained (900 mg, 65%) as oil.
Workup
- customTo the cooled reaction mixture
- extractionThe suspension was extracted with methylene chloride (2×30 mL)
- washThe organic layer was washed with water (2×25 mL) and brine (25 mL)
- dry with materialdried (Na2SO4)
- customthe solvent removed under reduced pressure
- customThe residue was purified by column chromatography with silica gel and methylene chloride/ethanol/ammonium hydroxide (100:8:1) as eluent
Sources & evidence
- ORD record
- ord-074e2c7c819d4669ab9f69312d2006ad
- Source dataset
- uspto-grants-2012_08
- Patent number
- US08242177B2
Reaction notes
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