Hydrochloric Acid → HCID 15491199, compound

HRID 1954693Notes

Reaction equation

HRID 1954693 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:15]2[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=2)([CH3:14])[CH2:9][CH2:10][C:11](O)=[O:12])=[CH:4][CH:3]=1.C(C1NC=CN=1)(C1NC=CN=1)=O.[CH2:34]([NH:41][CH2:42][C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1)[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1.Cl>O1CCCC1.C(OCC)(=O)C.O>[CH2:42]([N:41]([CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)[C:11](=[O:12])[CH2:10][CH2:9][C:8]([C:5]1[CH:4]=[CH:3][C:2]([OH:1])=[CH:7][CH:6]=1)([C:15]1[CH:16]=[CH:17][C:18]([OH:21])=[CH:19][CH:20]=1)[CH3:14])[C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 7656DibenzylamineHCID 671744,4-Bis(4-hydroxyphenyl)valeric acidHCID 5250894Bis-(1H-imidazol-2-YL)-methanone

Product 1

HCID 15491199HCID 15491199, compoundYield 40%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 4,4-bis-(4-hydroxyphenyl)pentanoic acid (2.00 g, 6.99 mmol) in 40 mL anhydrous tetrahydrofuran was treated with carbonyl diimidazole (3.76 g, 23.2 mmol) and the resulting solution heated at reflux under a N2 atmosphere for 24 hours. Dibenzylamine (5.38 mL, 28 mmol) was then added, and the reaction refluxed again for 48 hours. The reaction mixture was cooled and treated with 10% aqueous HCl solution (50 mL), followed by water (100 mL) and ethyl acetate (200 mL). The organic phase was collected and washed sequentially with water (100 mL) and brine (100 mL). The organic phase was dried (MgSO4), filtered and concentrate. The residue was purified by chromatography (silica gel, 50% ethyl acetate/hexane) to give the title compound (1.30 g, 40%) as a solid, mp=203-207° C.

Workup

  1. temperaturethe resulting solution heated
  2. temperatureat reflux under a N2 atmosphere for 24 hours
  3. temperaturethe reaction refluxed again for 48 hours
  4. temperatureThe reaction mixture was cooled
  5. customThe organic phase was collected
  6. washwashed sequentially with water (100 mL) and brine (100 mL)
  7. dry with materialThe organic phase was dried (MgSO4)
  8. filtrationfiltered
  9. concentrationconcentrate
  10. customThe residue was purified by chromatography (silica gel, 50% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-6bc889e23f6047229594d7649c1319c2
Source dataset
uspto-grants-2000_09
Patent number
US06124280

Reaction notes

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