Hydrogen Bromide → HCID 69227291, compound

HRID 1182023Notes

Reaction equation

HRID 1182023 reaction equation
[F:1][C:2]1([F:25])[C@@H:11]([CH2:12][O:13][C:14](=[O:16])[CH3:15])[O:10][C@H:5]([O:6]C(=O)C)[C@H:4]([O:17][C:18](=[O:20])[CH3:19])[C@H:3]1[O:21][C:22](=[O:24])[CH3:23].C(OCC)(=O)C.[BrH:32]>C(O)(=O)C>[Br:32][C@@:5]1([O:10][C@H:11]([CH2:12][O:13][C:14](=[O:16])[CH3:15])[C:2]([F:25])([F:1])[C@H:3]([O:21][C:22](=[O:24])[CH3:23])[C@H:4]1[O:17][C:18](=[O:20])[CH3:19])[OH:6]

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 8857Ethyl AcetateHCID 67119993HCID 67119993, compound

Product 1

HCID 69227291HCID 69227291, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

300 mg (0.8 mmol) of tetraacetate 46 are dissolved in 13 ml of 33% strength HBr in glacial acetic acid and left to stand at room temperature for 6 hours. The reaction solution is then poured into a mixture of 10 g of ice and 10 ml of ethyl acetate. The organic phase is washed twice more with aqueous NaCl solution, filtered through a little silica gel and concentrated. The residue is separated by chromatography on silica gel (ethyl acetate/heptane 1:1). 112 mg (35%) of 47 are obtained as a colorless solid. C12H15BrF2O7(389.15) MS(DCl): 389.2 (M+H+).

Workup

  1. waitleft
  2. washThe organic phase is washed twice more with aqueous NaCl solution
  3. filtrationfiltered through a little silica gel
  4. concentrationconcentrated
  5. customThe residue is separated by chromatography on silica gel (ethyl acetate/heptane 1:1)

Sources & evidence

ORD record
ord-b947ce5ae3e54317b3c7b3c212a0d6c5
Source dataset
uspto-grants-2007_10
Patent number
US07288528B2

Reaction notes

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