2,5-Dimethoxytetrahydrofuran → 3-(4-Hydroxyphenyl)-3-(1H-pyrrol-1-yl)propanoic acid

HRID 1993078Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1993078
CO[CH:3]1[CH2:7][CH2:6][CH:5](OC)O1.[NH2:10][CH:11]([C:16]1[CH:21]=[CH:20][C:19]([OH:22])=[CH:18][CH:17]=1)[CH2:12][C:13]([OH:15])=[O:14].C([O-])(=O)C.[Na+]>C(O)(=O)C>[OH:22][C:19]1[CH:18]=[CH:17][C:16]([CH:11]([N:10]2[CH:3]=[CH:7][CH:6]=[CH:5]2)[CH2:12][C:13]([OH:15])=[O:14])=[CH:21][CH:20]=1

Komponenten

5

Edukt 3

HCID 790982,5-DimethoxytetrahydrofuranHCID 4403113-Amino-3-(4-hydroxyphenyl)propanoic acidHCID 517045Sodium Acetate

Produkt 1

HCID 591327223-(4-Hydroxyphenyl)-3-(1H-pyrrol-1-yl)propanoic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

At 100° C., 2,5-dimethoxytetrahydrofuran (8.5 mmol) was added to a mixture of 3-amino-3-(4-hydroxyphenyl)propanoic acid (7.7 mmol) and sodium acetate (46 mmol) in acetic acid (34 mL). After stirring for 1 h, acetic acid was removed under reduced pressure. The residue was extracted with ethyl acetate (300 mL). The organic layer was washed with brine and dried over anhydrous Na2SO4 and concentrated. The residue was purified via column chromatography (10% methanol in dichloromethane) to compound 55.1. LC-MS (neg.) m/e: 230.2 (M−H).

Aufarbeitung

  1. customacetic acid was removed under reduced pressure
  2. extractionThe residue was extracted with ethyl acetate (300 mL)
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous Na2SO4
  5. concentrationconcentrated
  6. customThe residue was purified via column chromatography (10% methanol in dichloromethane) to compound 55.1

Quellen und Nachweise

ORD-Eintrag
ord-e4680af77fa74ac8ad506c74f984b27f
Quelldatensatz
uspto-grants-2010_01
Patentnummer
US07649110B2

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