Hydrogen Bromide → HCID 68580915, compound

HRID 644777Notes

Reaction equation

HRID 644777 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]([N:24]2[CH:28]=[C:27]([C:29]([O:31][CH3:32])=[O:30])[N:26]=[N:25]2)[C@H:6]1[O:7][C:8](=[O:10])[CH3:9])(=O)C.C(OC(=O)C)(=O)C.[BrH:40]>ClCCl.CC(O)=O>[C:8]([O:7][C@@H:6]1[C@@H:11]([N:24]2[CH:28]=[C:27]([C:29]([O:31][CH3:32])=[O:30])[N:26]=[N:25]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:40])(=[O:10])[CH3:9]

Participants

6

Reactant 3

HCID 260Hydrogen BromideHCID 7918Acetic AnhydrideHCID 68578563HCID 68578563, compound

Product 1

HCID 68580915HCID 68580915, compoundYield 46%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6344DichloromethaneSolvent2×

Procedure

1,2,4,6-Tetra-O-acetyl-3-deoxy-3-[4-(methoxycarbonyl)-1H-1,2,3-triazol-1-yl]-D-galactopyranose 23 (33 mg, 0.072 mmol) was dissolved in dichloromethane (1 ml) which had been dried over 4 Å molecular sieves. Acetic anhydride (14 l, 0.20 mmol) and HBr (0.2 ml of a 33% solution in AcOH) were added, and the mixture was stirred under N2 at room temperature. After 3 h 15 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. The residue was purified by flash column chromatography to give 24 (16 mg, 46%), which was used immediately in the synthesis of 25.

Workup

  1. customhad been dried over 4 Å molecular sieves
  2. washThe organic phase was washed with NaHCO3 (30 ml of a saturated aqueous solution)
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash column chromatography

Sources & evidence

ORD record
ord-dbaf5b04145b40d8973b06fb526c945c
Source dataset
uspto-grants-2010_04
Patent number
US07700763B2

Reaction notes

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