Hydrogen Bromide → HCID 59593754, compound

HRID 1474596Notes

Reaction equation

HRID 1474596 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]([Cl:25])=[C:21]([CH2:26]OC3C=CC=CC=3)[CH:20]=2)[O:7][C@@H:6]1[CH2:34][O:35][C:36](=[O:38])[CH3:37])(=[O:3])[CH3:2].[BrH:39].C([O-])([O-])=O.[K+].[K+]>C(O)(=O)C>[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]([Cl:25])=[C:21]([CH2:26][Br:39])[CH:20]=2)[O:7][C@@H:6]1[CH2:34][O:35][C:36](=[O:38])[CH3:37])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 11430Potassium CarbonateHCID 59593753HCID 59593753, compound

Product 1

HCID 59593754HCID 59593754, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

To a solution of (2R,3R,4R,5S,6S)-2-(acetoxymethyl)-6-(4-chloro-3-(phenoxymethyl)phenyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate (10.00 g, 18.22 mmol) in acetic acid (31 mL) was added HBr in acetic acid (45.55 mL, 2.5 mL/mmol) and the reaction mixture was stirred at r.t. for 18 h. After the completion of reaction as confirmed by TLC, the reaction mixture was neutralized by the addition of saturated K2CO3 at 0° C. and extracted with ethyl acetate (2×50 mL). The combined organic layers were washed with water (50 mL) and brine (50 mL) successively. The organic layer was dried over Na2SO4 and concentrated in vacuo to afford crude product which was purified by column chromatography (silica gel, 3:7 Ethyl acetate:Pet. Ether) to afford the title compound (7.9 g, 81%).

Workup

  1. customAfter the completion of reaction
  2. extractionextracted with ethyl acetate (2×50 mL)
  3. washThe combined organic layers were washed with water (50 mL) and brine (50 mL) successively
  4. dry with materialThe organic layer was dried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customto afford crude product which
  7. customwas purified by column chromatography (silica gel, 3:7 Ethyl acetate:Pet. Ether)

Sources & evidence

ORD record
ord-d48a961a2adc4b10bfc81d388616c38a
Source dataset
uspto-grants-2015_04
Patent number
US09018249B2

Reaction notes

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