Sodium Iodide → (2S)-2-Methoxy-3-{4-[3-(3-phenyl-benzofuran-6-yloxy)-prop-1-ynyl]-phenyl}-propionic acid

HRID 459076

Reaktionsgleichung

Reaktionsgleichung von HRID 459076
C([O:3][C:4](=[O:19])[C@@H:5]([O:17][CH3:18])[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]#[C:14][CH2:15]Cl)=[CH:9][CH:8]=1)C.[C:20]1([C:26]2[C:30]3[CH:31]=[CH:32][C:33]([OH:35])=[CH:34][C:29]=3[O:28][CH:27]=2)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.[Na+].[I-]>CN(C=O)C>[CH3:18][O:17][C@@H:5]([CH2:6][C:7]1[CH:8]=[CH:9][C:10]([C:13]#[C:14][CH2:15][O:35][C:33]2[CH:32]=[CH:31][C:30]3[C:26]([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)=[CH:27][O:28][C:29]=3[CH:34]=2)=[CH:11][CH:12]=1)[C:4]([OH:3])=[O:19]

Komponenten

5

Edukt 3

HCID 5238Sodium IodideHCID 122735253-Phenyl-benzofuran-6-olHCID 58822943(2S)-3-[4-(3-Chloro-prop-1-ynyl)-phenyl]-2-methoxy-propionic acid ethyl ester

Produkt 1

HCID 58822838(2S)-2-Methoxy-3-{4-[3-(3-phenyl-benzofuran-6-yloxy)-prop-1-ynyl]-phenyl}-propionic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A solution of (2S)-3-[4-(3-Chloro-prop-1-ynyl)-phenyl]-2-methoxy-propionic acid ethyl ester from Step A (0.071 mmol, 1 eq) in 0.7 ml of DMF in a 16×100 mm tube treated with 3-phenyl-6-hydroxybenzofurane (0.078 mmol, 1.1 eq) Cesium Carbonate (0.213 mmol 3 eq) and NaI (0.071 mmol, 1 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 C27H22O5 [M+H]+: 427.2.

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-da13f274d6c3495a92c57a5ab0b9f326
Quelldatensatz
uspto-grants-2007_03
Patentnummer
US07192982B2

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