4-Benzylphenol → (2S)-3-{4-[5-(4-Benzyl-phenoxy)-pent-1-ynyl]-phenyl}-2-methoxy-propionic acid

HRID 459094

Reaktionsgleichung

Reaktionsgleichung von HRID 459094
C([O:3][C:4](=[O:21])[CH:5]([O:19][CH3:20])[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]#[C:14][CH2:15][CH2:16][CH2:17]Br)=[CH:9][CH:8]=1)C.[CH:22]1[CH:23]=[CH:24][C:25]([CH2:28][C:29]2[CH:30]=[CH:31][C:32]([OH:35])=[CH:33][CH:34]=2)=[CH:26][CH:27]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[CH2:28]([C:29]1[CH:30]=[CH:31][C:32]([O:35][CH2:17][CH2:16][CH2:15][C:14]#[C:13][C:10]2[CH:9]=[CH:8][C:7]([CH2:6][C@H:5]([O:19][CH3:20])[C:4]([OH:3])=[O:21])=[CH:12][CH:11]=2)=[CH:33][CH:34]=1)[C:25]1[CH:24]=[CH:23][CH:22]=[CH:27][CH:26]=1

Komponenten

5

Edukt 3

HCID 75634-BenzylphenolHCID 10796Cesium carbonateHCID 694219733-[4-(5-Bromo-pent-1-ynyl)-phenyl]-2-methoxy-propionic acid ethyl ester

Produkt 1

HCID 58822670(2S)-3-{4-[5-(4-Benzyl-phenoxy)-pent-1-ynyl]-phenyl}-2-methoxy-propionic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A solution of 3-[4-(5-Bromo-pent-1-ynyl)-phenyl]-2-methoxy-propionic acid ethyl ester from Step A (0.1 mmol, 1 eq) in 0.7 ml of DMF in a 16×100 mm tube treated with 4-hydroxydiphenylmethane (0.11 mmol, 1.1 eq) and Cesium Carbonate (0.3 mmol, 3 eq) and stirred at room temperature overnight. The reactants were filtered and washed with DMF several times. The solvent was evaporated under vacuo and the residue reconstituted in a mixture of Ethanol (2 ml) and NaOH (1M) (1 ml) and stirred at room temperature until reaction is completed by HPLC-MS. Then HCl (1M) was added (until pH=3) and the solvent were eliminated under vacuo. The residue was reconstituted in CH2Cl2/H2O and filtered through a hidrofobic syringer. The organic layer was separated, concentrated and purified by HPLC-MS to get the title compound. MS(ES) for C28H28O4[M+NH4]+: 446.2.

Aufarbeitung

  1. filtrationThe reactants were filtered
  2. washwashed with DMF several times
  3. customThe solvent was evaporated under vacuo
  4. additionthe residue reconstituted in a mixture of Ethanol (2 ml) and NaOH (1M) (1 ml)
  5. stirringstirred at room temperature until reaction
  6. additionThen HCl (1M) was added (until pH=3)
  7. filtrationfiltered through a hidrofobic syringer
  8. customThe organic layer was separated
  9. concentrationconcentrated
  10. custompurified by HPLC-MS

Quellen und Nachweise

ORD-Eintrag
ord-c6e3361eb9e9459bb36ac4e54a7ea036
Quelldatensatz
uspto-grants-2007_03
Patentnummer
US07192982B2

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