Hydrochloric Acid → HCID 178467730, compound

HRID 1067685Notes

Reaction equation

HRID 1067685 reaction equation
C1(C(C2C=CC=CC=2)(C2C=CC=CC=2)[N:8]2[CH:12]=[C:11]([CH2:13][CH2:14][CH2:15]O)[N:10]=[CH:9]2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[OH:48][C:49]1[CH:54]=[CH:53][C:52]([CH2:55][CH2:56][C:57](=[O:59])[CH3:58])=[CH:51][CH:50]=1.N(C(OCC)=O)=NC(OCC)=O.Cl>C1COCC1.C(OCC)(=O)C>[NH:8]1[CH:12]=[C:11]([CH2:13][CH2:14][CH2:15][O:48][C:49]2[CH:50]=[CH:51][C:52]([CH2:55][CH2:56][C:57](=[O:59])[CH3:58])=[CH:53][CH:54]=2)[N:10]=[CH:9]1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 11776TriphenylphosphineHCID 216484-(4'-Hydroxyphenyl)-2-butanoneHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 108328403-(1-Trityl-1H-imidazol-4-YL)propan-1-OL

Product 1

HCID 178467730HCID 178467730, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

5 mmol of 3-(1-triphenylmethyl-1H-imidazol-4-yl)propanol, 6 mmol of triphenylphosphine and 5 mmol of 4-(4-hydroxyphenyl)-2-butanone are dissolved under nitrogen in the cold. 6 mmol of diethyl azodicarboxylate, dissolved in 4 ml of THF, are added and the reaction mixture is stirred at room temperature for 48 hours. After evacuation of the solvent under reduced pressure and column chromatography (eluent: ethyl acetate), the residue is dissolved in 10 ml THF and 30 ml of 2N HCl and heated to 70° C. for 2 hours. The solvent is evaporated off under reduced pressure and triphenylmethanol is extracted using diethyl ether. The aqueous phase is neutralized with potassium carbonate and the product extracted with diethyl ether. The ethereal solution is dried and evaporated to obtain an oil, which is crystallized as hydrogen maleate from diethyl ether and ethanol.

Workup

  1. additionare added
  2. customThe solvent is evaporated off under reduced pressure and triphenylmethanol
  3. extractionis extracted
  4. extractionthe product extracted with diethyl ether
  5. customThe ethereal solution is dried
  6. customevaporated
  7. customto obtain an oil, which
  8. customis crystallized as hydrogen maleate from diethyl ether and ethanol

Sources & evidence

ORD record
ord-829bc98544924ae5ae48fff9a7e78e03
Source dataset
uspto-grants-2001_06
Patent number
US06248765B1

Reaction notes

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