Hydrochloric Acid → HCID 11248177, compound

HRID 2375972Notes

Reaction equation

HRID 2375972 reaction equation
Cl.[CH2:2]([C:9]1[O:10][C:11]2[CH:42]=[CH:41][CH:40]=[CH:39][C:12]=2[C:13]=1[C:14]1[CH:38]=[CH:37][C:17]([C:18]2[CH:23]=[CH:22][C:21]([C:24](=[O:36])[CH2:25][CH:26]3C(=O)OC(C)(C)[O:28][C:27]3=[O:35])=[CH:20][CH:19]=2)=[CH:16][CH:15]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1>C1COCC1>[CH2:2]([C:9]1[O:10][C:11]2[CH:42]=[CH:41][CH:40]=[CH:39][C:12]=2[C:13]=1[C:14]1[CH:15]=[CH:16][C:17]([C:18]2[CH:23]=[CH:22][C:21]([C:24](=[O:36])[CH2:25][CH2:26][C:27]([OH:35])=[O:28])=[CH:20][CH:19]=2)=[CH:37][CH:38]=1)[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 60147144HCID 60147144, compound

Product 1

HCID 11248177HCID 11248177, compoundYield 63.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2N Hydrochloric acid (1 mL) was added to a stirred solution of 5-{2-[4′-(2-benzyl-benzofuran-3-yl)-biphen-4-yl]-2-oxoethyl}-2,2-dimethyl-[1,3]-dioxane-4,6-dione (200 mg, 0.36 mmol) in THF (10 mL), and the resultant solution was heated at 70° C. for 6 hrs and then cooled to room temperature and concentrated in vacuo. The resulting solid was redissolved in DMSO (10 mL), and heated to 150° C. for 3 hrs before being cooled to room temperature, and diluted with water (20 mL), and extracted with ethyl acetate (3×20 mL). The combined extract was washed with water (2×10 mL), brine (3×10 mL), dried over anhydrous MgSO4, filtered and concentrated in vacuo. Purification of the product by trituration and filtration from MeOH afforded the title compound as a white solid (105 mg, 62%). Rf: 0.20 (5% methanol in dichloromethane); 1H-NMR (CDCl3, 300 MHz): δ 8.10 (2H, d, J=8 Hz, Ar—H), 7.80 (5H, m, Ar—H), 7.62 (1H, d, J=8 Hz, Ar—H), 7.48 (1H, d, J=8 Hz, Ar—H), 7.29 (6H, m, Ar—H), 4.26 (2H, s, PhCH2), 3.86 (2H, t, J=6 Hz), 2.86 (2H, t, J=6 Hz); ESI-LCMS e/z calcd for C31H24O4: 460.527, found 461 (M+H)+.

Workup

  1. concentrationconcentrated in vacuo
  2. dissolutionThe resulting solid was redissolved in DMSO (10 mL)
  3. temperatureheated to 150° C. for 3 hrs
  4. temperaturebefore being cooled to room temperature
  5. additiondiluted with water (20 mL)
  6. extractionextracted with ethyl acetate (3×20 mL)
  7. extractionThe combined extract
  8. washwas washed with water (2×10 mL), brine (3×10 mL)
  9. dry with materialdried over anhydrous MgSO4
  10. filtrationfiltered
  11. concentrationconcentrated in vacuo
  12. customPurification of the product
  13. filtrationby trituration and filtration from MeOH

Sources & evidence

ORD record
ord-b1b40d4e8c1641409c7e16e9610b7a4f
Source dataset
uspto-grants-2008_12
Patent number
US07465825B2

Reaction notes

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