Boron tribromide → HCID 131715108, compound
Reaction equation
B(Br)(Br)Br.[CH2:5]([NH:9][C:10](=[S:42])[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][C@@H:21]1[CH2:38][C:37]2[CH:36]=[C:35]([O:39]C)[CH:34]=[CH:33][C:32]=2[C@@H:31]2[C@@H:22]1[C@H:23]1[C@@:27]([CH2:29][CH2:30]2)([CH3:28])[C@@H:26]([OH:41])[CH2:25][CH2:24]1)[CH2:6][CH2:7][CH3:8].C(=O)(O)[O-].[Na+]>C(Cl)Cl>[CH2:5]([NH:9][C:10](=[S:42])[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][C@@H:21]1[CH2:38][C:37]2[CH:36]=[C:35]([OH:39])[CH:34]=[CH:33][C:32]=2[C@@H:31]2[C@@H:22]1[C@H:23]1[C@@:27]([CH2:29][CH2:30]2)([CH3:28])[C@@H:26]([OH:41])[CH2:25][CH2:24]1)[CH2:6][CH2:7][CH3:8]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -20 °C
Procedure
Boron tribromide (0.5 ml.) was added to a stirred solution of the above thioamide (0.061 g.) in methylene chloride (3 ml.) which was cooled to -20° C., and the mixture was stirred at that temperature for 4 hours and then poured into saturated aqueous sodium bicarbonate solution (2 ml.). The mixture was extracted three times with methylene chloride (2 ml. each time) and the combined extracts were washed with water, dried and evaporated to dryness. The residue was purified by chromatography as described above and there was thus obtained as an oil N-n-butyl-11-(3,17β-dihydroxyoestra-1,3,5(10)-trien-7α-yl)thioundecanamide, the structure of which was confirmed by proton magnetic resonance and mass spectroscopy.
Workup
- extractionThe mixture was extracted three times with methylene chloride (2 ml
- washeach time) and the combined extracts were washed with water
- customdried
- customevaporated to dryness
- customThe residue was purified by chromatography
Sources & evidence
- ORD record
- ord-a329ea139cbf4b07b4e93133f39f33c0
- Source dataset
- uspto-grants-1987_04
- Patent number
- US04659516
Reaction notes
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