Ethyl 3-[{[4-({1-[5-(3-methoxyphenyl)-2-methylfuran-3-yl]-3-methylbutyl}amino)phenyl]carbonyl}(methyl)amino]propanoate → 3-[{[4-({1-[5-(3-Methoxyphenyl)-2-methylfuran-3-yl]-3-methylbutyl}amino)phenyl]carbonyl}(methyl)amino]propanoic acid

HRID 1877136Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1877136
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:9]2[O:13][C:12]([CH3:14])=[C:11]([CH:15]([NH:20][C:21]3[CH:26]=[CH:25][C:24]([C:27]([N:29]([CH3:37])[CH2:30][CH2:31][C:32]([O:34]CC)=[O:33])=[O:28])=[CH:23][CH:22]=3)[CH2:16][CH:17]([CH3:19])[CH3:18])[CH:10]=2)[CH:6]=[CH:7][CH:8]=1>C(O)C.CCCCCC>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:9]2[O:13][C:12]([CH3:14])=[C:11]([CH:15]([NH:20][C:21]3[CH:22]=[CH:23][C:24]([C:27]([N:29]([CH3:37])[CH2:30][CH2:31][C:32]([OH:34])=[O:33])=[O:28])=[CH:25][CH:26]=3)[CH2:16][CH:17]([CH3:19])[CH3:18])[CH:10]=2)[CH:6]=[CH:7][CH:8]=1

Komponenten

3

Edukt 1

HCID 68511355Ethyl 3-[{[4-({1-[5-(3-methoxyphenyl)-2-methylfuran-3-yl]-3-methylbutyl}amino)phenyl]carbonyl}(methyl)amino]propanoate

Produkt 1

HCID 595294013-[{[4-({1-[5-(3-Methoxyphenyl)-2-methylfuran-3-yl]-3-methylbutyl}amino)phenyl]carbonyl}(methyl)amino]propanoic acidAusbeute 92 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21879635Ethanol hexaneLösungsmittel

Versuchsvorschrift

Ethyl 3-[{[4-({1-[5-(3-methoxyphenyl)-2-methylfuran-3-yl]-3-methylbutyl}amino)phenyl]carbonyl}(methyl)amino]propanoate (1200 mg) which is a synthetic intermediate in Example 151 was dissolved in ethanol-hexane (6:4, volume ratio), and the solution was subjected to HPLC using CHIRALPAK AD (50 mmID×500 mL, manufactured by DAICEL CHEMICAL INDUSTRIES, LTD.) and eluted with ethanol-hexane (6:4, volume ratio) as mobile phase at 30° C., a flow rate 60 mL/min. The fractions showing a peak with retention time 11.1 min were collected, and concentrated. The obtained amorphous compound (598 mg) was dissolved in ethanol (5 mL) and tetrahydrofuran (5 mL), lithium hydroxide (2.5 mL) was added, and the mixture was stirred at room temperature for 1 hr. The solvent was evaporated under reduced pressure, and water (20 mL) was added. The mixture was neutralized with 1N hydrochloric acid under ice-cooling, and stirred for 1 hr. The resulting precipitate was collected by filtration and dried to give the title compound (518 mg, 92%).

Aufarbeitung

  1. washeluted with ethanol-hexane (6:4, volume ratio) as mobile phase at 30° C.
  2. customwere collected
  3. concentrationconcentrated
  4. dissolutionThe obtained amorphous compound (598 mg) was dissolved in ethanol (5 mL)
  5. additiontetrahydrofuran (5 mL), lithium hydroxide (2.5 mL) was added
  6. customThe solvent was evaporated under reduced pressure, and water (20 mL)
  7. additionwas added
  8. temperaturecooling
  9. stirringstirred for 1 hr
  10. filtrationThe resulting precipitate was collected by filtration
  11. customdried

Quellen und Nachweise

ORD-Eintrag
ord-efe6c87bae92452b9a2acb7e42744725
Quelldatensatz
uspto-grants-2012_11
Patentnummer
US08309580B2

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