Boron tribromide → HCID 22177684, compound
Reaction equation
[CH2:1]([N:3]([C:8]1[N:13]2[N:14]=[C:15]([CH2:26][O:27]C)[C:16]([C:17]3[CH:22]=[CH:21][C:20]([O:23]C)=[CH:19][C:18]=3[CH3:25])=[C:12]2[N:11]=[C:10]2[CH2:29][CH2:30][CH2:31][C:9]=12)[CH2:4][CH2:5][CH2:6][CH3:7])[CH3:2].B(Br)(Br)Br.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[CH2:1]([N:3]([C:8]1[N:13]2[N:14]=[C:15]([CH2:26][OH:27])[C:16]([C:17]3[CH:22]=[CH:21][C:20]([OH:23])=[CH:19][C:18]=3[CH3:25])=[C:12]2[N:11]=[C:10]2[CH2:29][CH2:30][CH2:31][C:9]=12)[CH2:4][CH2:5][CH2:6][CH3:7])[CH3:2]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -30 °C
Procedure
To a solution of the compound prepared in Example 2(1) (506 mg) in methylene chloride (14 ml) which was cooled to −78° C., 1M boron tribromide in methylene chloride (12 ml) was added. The mixture was stirred for 30 minutes at −78° C. and for 5 hours at −30° C. The reaction mixture was poured into a saturated aqueous solution of sodium bicarbonate and the resultant solution was extracted with ethyl acetate. The organic layer was washed with a saturated aqueous solution of sodium chloride, dried over anhydrous sodium sulfate and concentrated. The residue was purified by column chromatography on silica gel (n-hexane:ethyl acetate=1:1→2:3) to give the title compound (303 mg) having the following physical data
Workup
- extractionthe resultant solution was extracted with ethyl acetate
- washThe organic layer was washed with a saturated aqueous solution of sodium chloride
- dry with materialdried over anhydrous sodium sulfate
- concentrationconcentrated
- customThe residue was purified by column chromatography on silica gel (n-hexane:ethyl acetate=1:1→2:3)
Sources & evidence
- ORD record
- ord-ff5d13eae21c40019ce3d3102fa99ab1
- Source dataset
- uspto-grants-2008_12
- Patent number
- US07459459B2
Reaction notes
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