Benzyl Bromide → HCID 86714024, compound
Reaction equation
[CH2:1]([O:4][C:5]1[CH:10]=[C:9]([Cl:11])[C:8]([CH2:12][C:13]2[CH:18]=[CH:17][C:16]([O:19][CH2:20][CH3:21])=[CH:15][CH:14]=2)=[CH:7][C:6]=1[C@H:22]1[C@H:27]([OH:28])[C@@H:26]([OH:29])[C@H:25]([OH:30])[C@@H:24]([CH2:31][OH:32])[O:23]1)[CH:2]=[CH2:3].[CH2:33](Br)[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1.[H-].[Na+].[NH4+].[Cl-]>C1COCC1.CN(C=O)C>[CH2:1]([O:4][C:5]1[CH:10]=[C:9]([Cl:11])[C:8]([CH2:12][C:13]2[CH:18]=[CH:17][C:16]([O:19][CH2:20][CH3:21])=[CH:15][CH:14]=2)=[CH:7][C:6]=1[C@H:22]1[C@H:27]([O:28][CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[C@@H:26]([O:29][CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[C@H:25]([O:30][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C@@H:24]([CH2:31][O:32][CH2:22][C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][CH:5]=2)[O:23]1)[CH:2]=[CH2:3]Participants
6
Procedure
To a solution of the crude compound 25-1 and benzyl bromide (2.6 mL, 21.6 mmol) in THF/DMF (30 mL/10 mL) was added NaH (60% dispersion in mineral oil, 1.3 g, 32.4 mmol) portionwise at 0° C. The reaction mixture was gradually raised to room temperature and stirred at r.t. for 15 hour. The mixture was cooled to 0° C. and aqueous saturated NH4Cl solution (150 mL) was added to the mixture. The mixture was extracted with EtOAc (100 mL). The organic layer was washed with brine, dried over anhydrous MgSO4, filtered and concentrated in vacuo. The residue was purified using normal phase column chromatography to provide the desired product 26 (1.50 g, 85% (2-steps)).
Workup
- temperatureThe mixture was cooled to 0° C.
- extractionThe mixture was extracted with EtOAc (100 mL)
- washThe organic layer was washed with brine
- dry with materialdried over anhydrous MgSO4
- filtrationfiltered
- concentrationconcentrated in vacuo
- customThe residue was purified
Sources & evidence
- ORD record
- ord-7b9b8bfbdf1d4146b5c661b8a7e04b7f
- Source dataset
- uspto-grants-2015_05
- Patent number
- US09034921B2
Reaction notes
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