Hydrochloric Acid → HCID 11203656, compound

HRID 900487Notes

Reaction equation

HRID 900487 reaction equation
Cl.[CH2:2]([C:9]1([CH2:19][C:20]([C:22]2[CH:27]=[CH:26][C:25]([C:28]3[CH:33]=[CH:32][C:31]([C:34]4[C:38]5[CH:39]=[CH:40][CH:41]=[CH:42][C:37]=5[O:36][C:35]=4[CH2:43][C:44]4[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=4)=[CH:30][CH:29]=3)=[CH:24][CH:23]=2)=[O:21])C(=O)OC(C)(C)[O:11][C:10]1=[O:18])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1>C1COCC1>[CH2:2]([CH:9]([CH2:19][C:20]([C:22]1[CH:27]=[CH:26][C:25]([C:28]2[CH:33]=[CH:32][C:31]([C:34]3[C:38]4[CH:39]=[CH:40][CH:41]=[CH:42][C:37]=4[O:36][C:35]=3[CH2:43][C:44]3[CH:45]=[CH:46][CH:47]=[CH:48][CH:49]=3)=[CH:30][CH:29]=2)=[CH:24][CH:23]=1)=[O:21])[C:10]([OH:18])=[O:11])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 60147146HCID 60147146, compound

Product 1

HCID 11203656HCID 11203656, compoundYield 37.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2 N Hydrochloric acid (1 mL) was added to a stirred solution of 5-benzyl-5-(2-[4′-(2-benzylbenzofuran-3-yl)-biphen-4-yl]-2-oxoethyl)-2,2-dimethyl-[1,3]dioxane-4,6-dione (200 mg) in THF (5 mL), and the resultant solution was heated at 70° C. for 6 h and then cooled to room temperature and concentrated in vacuo. The resulting solid was redissolved in DMSO (5 mL), and heated to 150° C. for 3 h 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), sat'd aq NaCl (3×10 mL), dried over anhyd MgSO4, filtered and concentrated in vacuo. Purification by trituration and filtration from MeOH afforded the title compound as a pale yellow solid (65 mg).

Workup

  1. concentrationconcentrated in vacuo
  2. dissolutionThe resulting solid was redissolved in DMSO (5 mL)
  3. temperatureheated to 150° C. for 3 h
  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)
  9. dry with materialdried over anhyd MgSO4
  10. filtrationfiltered
  11. concentrationconcentrated in vacuo
  12. customPurification
  13. filtrationby trituration and filtration from MeOH

Sources & evidence

ORD record
ord-7110871b3c7e41fca720825c9316ac5b
Source dataset
uspto-grants-2008_04
Patent number
US07358364B2

Reaction notes

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