Phenol → (2S)-2-methoxy-3-[4-(3-phenoxy propoxy)-phenyl]-propionic acid

HRID 459304

Reaktionsgleichung

Reaktionsgleichung von HRID 459304
C([O:3][C:4](=[O:20])[C@@H:5]([O:18][CH3:19])[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:14][CH2:15][CH2:16]Br)=[CH:9][CH:8]=1)C.[C:21]1([OH:27])[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>>[CH3:19][O:18][C@@H:5]([CH2:6][C:7]1[CH:8]=[CH:9][C:10]([O:13][CH2:14][CH2:15][CH2:16][O:27][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[CH:11][CH:12]=1)[C:4]([OH:3])=[O:20]

Komponenten

4

Edukt 3

HCID 996PhenolHCID 10796Cesium carbonateHCID 58822859(2S)-3-[4-(3-Bromopropoxy)-phenyl]-2-methoxy-propionic acid ethyl ester

Produkt 1

HCID 58822897(2S)-2-methoxy-3-[4-(3-phenoxy propoxy)-phenyl]-propionic acid

Versuchsvorschrift

A solution of (2S)-3-[4-(3-bromo-propoxy)-phenyl]-2-methoxy-propionic acid ethyl ester (Example 284, Step 2) (0.1 mmol, 32 mg) in 0.7 ml of DM in a 16×100 mm tube was treated with phenol (0.15 mmol, 15 mg), cesium carbonate (0.3 mmol, 95 mg). The mixture was stirred at room temperature overnight and the reactants were filtered and washed with DMF a several times. The solvent was evaporated under vacuum, and the residue was reconstituted in a mixture of ethanol (2 ml) and NaOH (1M, 1 ml), which was stirred at room temperature until temperature until reaction was completed by HPLC-MS. Upon completion, HCl (1M) was added pH=3) and the solvents were eliminated under vacuum. 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 afford the title compound as a colorless oil. MS (ES) for C19H22O5 [M+NH4]+: 348.4.

Aufarbeitung

  1. filtrationthe reactants were filtered
  2. washwashed with DMF a several times
  3. customThe solvent was evaporated under vacuum
  4. additionthe residue was reconstituted in a mixture of ethanol (2 ml) and NaOH (1M, 1 ml), which
  5. stirringwas stirred at room temperature until temperature until reaction
  6. additionUpon completion, HCl (1M) was added pH=3) and the solvents
  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-07a75bae0a2a4091b1f4a37985f7cb95
Quelldatensatz
uspto-grants-2007_03
Patentnummer
US07192982B2

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