Potassium Hydroxide → HCID 25168702, compound

HRID 1175303Notes

Reaction equation

HRID 1175303 reaction equation
[Cl:1][C:2]1[C:7]([CH2:8][C:9]2[CH:14]=[CH:13][C:12]([CH2:15][CH3:16])=[CH:11][CH:10]=2)=[CH:6][C:5]([C@H:17]2[C@H:22]([OH:23])[C@@H:21]([OH:24])[C@H:20]([OH:25])[C@@H:19]([CH2:26][OH:27])[O:18]2)=[C:4]([CH2:28][O:29][CH2:30][CH:31](Br)[CH2:32]Br)[CH:3]=1.[OH-].[K+]>C(O)C>[Cl:1][C:2]1[C:7]([CH2:8][C:9]2[CH:10]=[CH:11][C:12]([CH2:15][CH3:16])=[CH:13][CH:14]=2)=[CH:6][C:5]([C@H:17]2[C@H:22]([OH:23])[C@@H:21]([OH:24])[C@H:20]([OH:25])[C@@H:19]([CH2:26][OH:27])[O:18]2)=[C:4]([CH2:28][O:29][CH2:30][C:31]#[CH:32])[CH:3]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 68742663HCID 68742663, compound2×

Product 1

HCID 25168702HCID 25168702, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of (2S,3R,4R,5S,6R)-2-(4-chloro-2-((2,3-dibromopropoxy)methyl)-5-(4-ethylbenzyl)phenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol (53.3 mg, 0.086 mmol) (prepared by bromination of compound I) in anhydrous ethanol (1.0 mL) was added potassium hydroxide (10.6 mg). The reaction mixture was refluxed and monitored by LC-MS. After 6 h, LC-MS showed the reaction was complete. The reaction mixture was concentrated and the residue was partitioned between EtOAc and water, the organic layer was separated, washed 2× with 1N HCl, 3× with brine, and dried over Na2SO4. Concentration gave the crude product, which was purified by preparative HPLC to yield 21 mg of title compound as a white solid. 1H-NMR (CD3OD, 400 MHz) δ 7.48 (s, 1H), 7.42 (s, 1H), 7.11 (s, 4H), 4.85 (d, J=12.0 Hz, 1H), 4.62 (d, J=12.0 Hz, 1H), 4.51 (d, J=9.2 Hz, 1H), 4.23 (s, 2H), 4.10 (d, J=14.8 Hz, 1H), 4.05 (d, J=14.8 Hz, 1H), 3.88 (d, J=12.4 Hz, 1H), 3.71-3.67 (m, 1H), 3.52-3.41 (m, 4H), 2.94 (s, 1H), 2.60 (q, J=7.6 Hz, 2H), 1.21 (t, J=7.6 Hz, 3H); LC-MS (m/z) 461 [(M+1)+], 515 [(M+45)−].

Workup

  1. temperatureThe reaction mixture was refluxed
  2. concentrationThe reaction mixture was concentrated
  3. customthe residue was partitioned between EtOAc and water
  4. customthe organic layer was separated
  5. washwashed 2× with 1N HCl, 3× with brine
  6. dry with materialdried over Na2SO4
  7. concentrationConcentration
  8. customgave the crude product, which
  9. customwas purified by preparative HPLC

Sources & evidence

ORD record
ord-2e57c00381a74296b1c258e8c6e20d51
Source dataset
uspto-grants-2010_11
Patent number
US07838498B2

Reaction notes

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