Benzyl Bromide → HCID 70389672, compound
Reaction equation
O1CCCC1.C[O:7][C:8](=[O:37])[C@:9]([NH2:36])([C@@H:21]([CH2:29][C:30](=[O:35])[CH:31]=[CH:32][CH2:33][CH3:34])[O:22][CH:23]1[CH2:28][CH2:27][CH2:26][CH2:25][O:24]1)[NH:10][C:11]([O:13][Si](C(C)(C)C)(C)C)=[O:12].[CH2:38](Br)[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>CCOCC.CCCCCC.O>[CH2:38]([O:13][C:11]([NH:10][C@:9]([NH2:36])([C:8]([OH:7])=[O:37])[C@@H:21]([CH2:29][C:30](=[O:35])[CH:31]=[CH:32][CH2:33][CH3:34])[O:22][CH:23]1[CH2:28][CH2:27][CH2:26][CH2:25][O:24]1)=[O:12])[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1Participants
7
Conditions
- Temperature
- 0 °C
Procedure
To a tetrahydrofuran solution (1.0 ml) of the compound prepared in Example 2 (45.8 mg, 0.09 mmol), were successively added dropwise at 0° C. in a nitrogen atmosphere benzyl bromide (0.021 ml, 0.18 mmol) and a tetrahydrofuran solution of tetrabutyl ammonium fluoride (0.090 ml, 0.09 mmol). The mixture was stirred for 1 hour at 0° C., poured into water and extracted with ether. The ether layer was dried over anhydrous magnesium sulfate and the solvent was distilled off under vacuum. The resulting reaction mixture was subjected to column chromatography (ether/hexane=1/1) to give 31.2 mg of the titled compound (yield, 78% based on the starting materials used in Example 2).
Workup
- extractionextracted with ether
- dry with materialThe ether layer was dried over anhydrous magnesium sulfate
- distillationthe solvent was distilled off under vacuum
- customThe resulting reaction mixture
Sources & evidence
- ORD record
- ord-38afecbd9b314add85c7a3aea5d0f5fd
- Source dataset
- uspto-grants-1989_06
- Patent number
- US04837349
Reaction notes
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