Hydrogen Bromide → HCID 67404620, compound
Reaction equation
C(O[CH:5]1[O:18][C@H:17]([CH2:19][O:20][C:21](=[O:23])[CH3:22])[C@H:12]([O:13][C:14](=[O:16])[CH3:15])[C@H:11]([NH:24][C:25](=[O:36])[C:26]2[CH:31]=[C:30]([O:32][CH3:33])[CH:29]=[C:28]([O:34][CH3:35])[CH:27]=2)[C@H:6]1[O:7][C:8](=[O:10])[CH3:9])(=O)C.C(OC(=O)C)(=O)C.[BrH:44]>ClCCl>[C:8]([O:7][C@@H:6]1[C@@H:11]([NH:24][C:25](=[O:36])[C:26]2[CH:27]=[C:28]([O:34][CH3:35])[CH:29]=[C:30]([O:32][CH3:33])[CH:31]=2)[C@@H:12]([O:13][C:14](=[O:16])[CH3:15])[C@@H:17]([CH2:19][O:20][C:21](=[O:23])[CH3:22])[O:18][C@@H:5]1[Br:44])(=[O:10])[CH3:9]Participants
5
Procedure
1,2,4,6-Tetra-O-acetyl-3-deoxy-3-(3,5-dimethoxybenzamido)-D-galactopyranose 4 (50 mg, 0.098 mmol) was dissolved in dichloromethane (1 ml) which had been dried over 4 Å molecular sieves. Acetic anhydride (18 μl, 0.20 mmol) and HBr (0.2 ml, 33% in AcOH) were added, and the mixture was stirred under N2 at room temperature. After 2 h 30 min, the reaction mixture was diluted with dichloromethane (30 ml) and poured into ice-water (30 ml). The organic phase was washed with NaHCO3 (30 ml of a saturated aqueous solution), dried (MgSO4), filtered and concentrated in vacuo to give 2,4,6-tri-O-acetyl-3-deoxy-3-(3,5-dimethoxybenzamido)-α-D-galactopyranosyl bromide 9, which was used without further purification.
Workup
- customhad been dried over 4 Å molecular sieves
- washThe organic phase was washed with NaHCO3 (30 ml of a saturated aqueous solution)
- dry with materialdried (MgSO4)
- filtrationfiltered
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-a6da6e937d67498088a2bfd3dd05f861
- Source dataset
- uspto-grants-2009_12
- Patent number
- US07638623B2
Reaction notes
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