Hydrochloric Acid → HCID 70363655, compound

HRID 2166482Notes

Reaction equation

HRID 2166482 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C@H:10]([N:14]2[C:23](=[O:24])[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[C:15]2=[O:16])[C:11](O)=[O:12])=[CH:5][CH:4]=1.P(Cl)(Cl)(Cl)(Cl)Cl.[CH3:31][O:32][C:33]1[C:34](=[CH:37][CH:38]=[CH:39][CH:40]=1)[O:35][CH3:36].Cl>ClCCCl.[Fe](Cl)(Cl)Cl>[CH3:31][O:32][C:33]1[CH:40]=[C:39]([CH:9]([C:6]2[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=2)[C@@H:10]([C:11]([C@@H:10]([N:14]2[C:15](=[O:16])[C:17]3=[CH:18][CH:19]=[CH:20][CH:21]=[C:22]3[C:23]2=[O:24])[CH:9]([C:6]2[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)[C:38]2[CH:39]=[CH:40][C:33]([O:32][CH3:31])=[C:34]([O:35][CH3:36])[CH:37]=2)=[O:12])[N:14]2[C:15](=[O:16])[C:17]3=[CH:18][CH:19]=[CH:20][CH:21]=[C:22]3[C:23]2=[O:24])[CH:38]=[CH:37][C:34]=1[O:35][CH3:36]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 7043VeratroleHCID 24819Phosphorus pentachlorideHCID 7150570HCID 7150570, compound

Product 1

HCID 70363655HCID 70363655, compoundYield 44.8%

Reagents, catalysts & solvents 2

HCID 24380Iron chloride (FeCl3)CatalystHCID 111,2-DichloroethaneSolvent3×

Conditions

Temperature
0 °C

Procedure

A solution of 3.25 g (10.0 mmole) N-phthaloyl-0-methyl-(S)-tyrosine in 50 ml 1,2-dichloroethane was combined with 2.29 g (11.0 mmole) phosphorus pentachloride at 0° C. and agitated at first for 30 minutes at 0° C. and then for 16 hours at room temperature. After the addition of another 50 ml 1,2-dichloroethane, a tenth of the solution was rapidly added to an agitated solution of 1.38 g (10.0 mmole) catechol dimethylether and 160 mg iron-(III)-chloride (10 mole percent) in 70 ml 1,2-dichloroethane. The reaction mixture was heated to 50° C. and the remaining solution of acid chloride was added dropwise in a continuous manner over 12 hours. The mixture was agitated 12 hours further at 50° C. and then cooled down to 0° C. 100 ml 1N hydrochloric acid cooled down to 0° C. were added and the mixture was agitated for 24 hours at room temperature. The aqueous phase was separated off and extracted twice with 40 ml methylene chloride per extraction. The combined organic phases were washed with 150 ml saturated, aqueous sodium hydrogen carbonate solution, then with 100 ml water, and dried over sodium sulfate. After removal of the solvent at 40° C. under reduced pressure, the raw product was chromatographed over a silica gel column. 1.93 g (43 % of theory) (S)-3,4-dimethoxyphenyl-[2-(4-methoxyphenyl)-1-phthalimidoethyl]-ketone of reagent purity were obtained as oil.

Workup

  1. waitfor 16 hours at room temperature
  2. temperatureThe reaction mixture was heated to 50° C.
  3. stirringThe mixture was agitated 12 hours further at 50° C.
  4. temperaturecooled down to 0° C
  5. additionwere added
  6. stirringthe mixture was agitated for 24 hours at room temperature
  7. customThe aqueous phase was separated off
  8. extractionextracted twice with 40 ml methylene chloride per extraction
  9. washThe combined organic phases were washed with 150 ml saturated
  10. dry with materialaqueous sodium hydrogen carbonate solution, then with 100 ml water, and dried over sodium sulfate
  11. customAfter removal of the solvent at 40° C. under reduced pressure
  12. customthe raw product was chromatographed over a silica gel column

Sources & evidence

ORD record
ord-ca3e4b4c89c14647b450314493ce48ed
Source dataset
uspto-grants-1990_07
Patent number
US04945168

Reaction notes

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