Hydrogen Bromide → HCID 86691704, compound

HRID 1022474Notes

Reaction equation

HRID 1022474 reaction equation
[C:1]([O:4][C@H:5]1[C@H:10]([O:11][C:12](=[O:14])[CH3:13])[C@@H:9]([O:15][C:16](=[O:18])[CH3:17])[C@H:8]([C:19]2[CH:24]=[CH:23][C:22]([CH2:25][CH3:26])=[C:21]([CH2:27][C:28]3[CH:29]=[C:30]4[C:35](=[CH:36][CH:37]=3)[O:34][CH2:33][CH2:32][CH2:31]4)[CH:20]=2)[O:7][CH:6]1OC(=O)C)(=[O:3])[CH3:2].C(=O)(O)[O-].[Na+].[BrH:47]>C(O)(=O)C.ClCCl>[C:12]([O:11][C@@H:10]1[C@@H:9]([O:15][C:16](=[O:18])[CH3:17])[C@H:8]([C:19]2[CH:24]=[CH:23][C:22]([CH2:25][CH3:26])=[C:21]([CH2:27][C:28]3[CH:29]=[C:30]4[C:35](=[CH:36][CH:37]=3)[O:34][CH2:33][CH2:32][CH2:31]4)[CH:20]=2)[O:7][CH:6]([Br:47])[C@H:5]1[O:4][C:1](=[O:3])[CH3:2])(=[O:14])[CH3:13]

Participants

6

Reactant 3

HCID 260Hydrogen BromideHCID 516892Sodium BicarbonateHCID 86691705HCID 86691705, compound

Product 1

HCID 86691704HCID 86691704, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6344DichloromethaneSolvent2×

Procedure

Step-I: Acetic acid (3S,4R,5S,6S)-3,4,5-triacetoxy-6-(3-chroman-6-ylmethyl-4-ethyl-phenyl)-tetrahydro-pyran-2-yl ester (300 mg) was taken in 33% HBr in acetic acid (1.2 ml) and stirred for 1 h at room temperature. To this was added dichloromethane (2 ml) and stirred for additional 30 min. This was diluted with dichloromethane (5 ml), poured into crushed ice and neutralized with sodium bicarbonate. Organic layer was separated, extracted with DCM (8 ml×2), combined organic layers were washed with water (10 ml×2), brine (10 ml), dried over sodium sulfate, concentrated to give 250 mg of acetic acid (3S,4R,5S,6S)-4,5-diacetoxy-2-bromo-6-(3-chroman-6-ylmethyl-4-ethyl-phenyl)-tetrahydro-pyran-3-yl ester.

Workup

  1. stirringstirred for additional 30 min
  2. additionpoured
  3. custominto crushed ice
  4. customOrganic layer was separated
  5. extractionextracted with DCM (8 ml×2)
  6. washwere washed with water (10 ml×2), brine (10 ml)
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-f13b05fcf1b648b58a9bdb20f0a0131c
Source dataset
uspto-grants-2014_05
Patent number
US08722633B2

Reaction notes

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