Potassium Carbonate → HCID 117985977, compound

HRID 1055621Notes

Reaction equation

HRID 1055621 reaction equation
C([O:4][C@H:5]1[C@H:11](CC([O-])=O)[C@@H:10]([O:16]C(=O)C)[C@:9]2([C:21]3[CH:26]=[CH:25][C:24]([Cl:27])=[C:23]([CH:28]([C:30]4[CH:35]=[CH:34][C:33]([O:36][CH2:37][CH3:38])=[CH:32][CH:31]=4)[OH:29])[CH:22]=3)[O:20][C@@:6]1([CH:39]([O:41]C(=O)C)[CH3:40])[CH2:7][O:8]2)(=O)C.C(=O)([O-])[O-:46].[K+].[K+]>CO>[Cl:27][C:24]1[CH:25]=[CH:26][C:21]([C@@:9]23[O:20][C@@:6]([CH:39]([OH:41])[CH3:40])([CH2:7][O:8]2)[C@@H:5]([OH:4])[C@H:11]([OH:46])[C@H:10]3[OH:16])=[CH:22][C:23]=1[CH:28]([C:30]1[CH:35]=[CH:34][C:33]([O:36][CH2:37][CH3:38])=[CH:32][CH:31]=1)[OH:29]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 131736406HCID 131736406, compound

Product 1

HCID 117985977HCID 117985977, compoundYield 20.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of [(1R,2S,3S,4R,5S)-2,4-diacetoxy-1-(1-acetoxyethyl)-5-[4-chloro-3-[(4-ethoxyphenyl)-hydroxy-methyl]phenyl]-6,8-dioxabicyclo[3.2.1]octan-3-yl]acetate 29d (316 mg, 0.5 mmol) in methanol (20 mL) was added potassium carbonate (344 mg, 2.5 mmol) at room temperature. The mixture was stirred at room temperature for 2 hours. Part of the solvent was removed in vacuo. The residue was extracted with ethyl acetate (10 mL×2). The combined organic layers were washed with water (10 mL×2) and then saturated aqueous sodium chloride (10 mL×2), dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated in vacuo. The residue was purified by silica gel chromatography eluted with EtOAc to give the title compound 29 as a white solid (47 mg, 20.0%, HPLC: 99.2%). The compound was characterized by the following spectroscopic data: 1H NMR (400 MHz, DMSO-d6) δ (ppm): 7.84 (s, 1H), 7.32 (d, 2H), 7.19 (d, 2H), 6.84 (d, 2H), 5.93 (d, 1H), 5.90 (d, 1H), 5.31 (d, 1H), 5.02 (d, 1H), 4.91 (d, 1H), 4.65 (d, 1H), 4.04 (m, 1H), 4.01-3.96 (m, 2H), 3.88-3.82 (m, 1H), 3.79 (d, 1H), 3.61-3.55 (m, 1H), 3.46 (d, 1H), 3.44-3.39 (m, 1H), 1.30 (t, 3H), 1.17 (d, 3H); and MS (ESI, pos. ion) m/z: 5112[M+HCOO]−.

Workup

  1. customPart of the solvent was removed in vacuo
  2. extractionThe residue was extracted with ethyl acetate (10 mL×2)
  3. washThe combined organic layers were washed with water (10 mL×2)
  4. dry with materialsaturated aqueous sodium chloride (10 mL×2), dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated in vacuo
  7. customThe residue was purified by silica gel chromatography
  8. washeluted with EtOAc

Sources & evidence

ORD record
ord-548416b900674b7492779500a5d47bee
Source dataset
uspto-grants-2016_07
Patent number
US09394329B2

Reaction notes

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