Formic Acid → HCID 54219284, Verbindung

HRID 987319Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 987319
Cl.[NH2:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][O:11][C:12]2[CH:17]=[CH:16][C:15]([CH2:18][C@H:19]([O:23][CH2:24][CH3:25])[C:20]([OH:22])=[O:21])=[CH:14][CH:13]=2)=[CH:5][CH:4]=1.[CH:26](O)=[O:27].C(OC(=O)C)(=O)C>O1CCCC1>[CH2:24]([O:23][C@@H:19]([CH2:18][C:15]1[CH:16]=[CH:17][C:12]([O:11][CH2:10][CH2:9][C:6]2[CH:5]=[CH:4][C:3]([NH:2][CH:26]=[O:27])=[CH:8][CH:7]=2)=[CH:13][CH:14]=1)[C:20]([OH:22])=[O:21])[CH3:25]

Komponenten

5

Edukt 3

HCID 284Formic AcidHCID 7918Acetic AnhydrideHCID 86595065HCID 86595065, Verbindung

Produkt 1

HCID 54219284HCID 54219284, VerbindungAusbeute 62 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

3-{4-[2-(4-Aminophenyl)ethoxy]phenyl}-(S)-2-ethoxypropanoic acid hydro chloride (described in Example 56a) (0.115 g, 0.314 mmole) in tetrahydrofuran (3 ml) was mixed with a mixture of formic acid (0.5 ml) and acetic anhydride (0.3 ml). The resulting mixture was stirred at room temperature overnight. Tetrahydrofuran was evaporated. Ethyl acetate and water were added into the residue. The phases were separated. The organic phase was washed with brine, dried with magnesium sulfate and the solvent was evaporated. Chromatography of the residue on silica gel (Isolute, SI) using dichloromethane, then methanol/dichloromethane (1%), followed by methanol/dichloromethane (2%) as eluants gave 0.07 g (yield 62%) of (S)-2-ethoxy-3-(4-{[4-(formylamino)phenethyl]oxy}phenyl)propanoic acid.

Aufarbeitung

  1. customTetrahydrofuran was evaporated
  2. additionEthyl acetate and water were added into the residue
  3. customThe phases were separated
  4. washThe organic phase was washed with brine
  5. dry with materialdried with magnesium sulfate
  6. customthe solvent was evaporated

Quellen und Nachweise

ORD-Eintrag
ord-5149462b2a9b460cbd32070d14319823
Quelldatensatz
uspto-grants-2003_10
Patentnummer
US06630600B1

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