Sodium Hydroxide → 2-((3S,5R,6S)-3-allyl-5-(3-chlorophenyl)-6-(4-chlorophenyl)-3-methyl-2-oxopiperidin-1-yl)butanoic acid

HRID 1048436Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1048436
[CH2:1]([C@@:4]1([CH3:32])[CH2:9][C@H:8]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([Cl:16])[CH:11]=2)[C@@H:7]([C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=2)[N:6]([C@@H:24]([CH2:29][CH3:30])[C:25]([O:27]C)=[O:26])[C:5]1=[O:31])[CH:2]=[CH2:3].[OH-].[Na+]>C1COCC1.O>[CH2:1]([C@@:4]1([CH3:32])[CH2:9][C@H:8]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([Cl:16])[CH:11]=2)[C@@H:7]([C:17]2[CH:18]=[CH:19][C:20]([Cl:23])=[CH:21][CH:22]=2)[N:6]([CH:24]([CH2:29][CH3:30])[C:25]([OH:27])=[O:26])[C:5]1=[O:31])[CH:2]=[CH2:3]

Komponenten

5

Edukt 2

HCID 14798Sodium HydroxideHCID 58573915(S)-Methyl 2-((3S,5R,6S)-3-allyl-5-(3-chlorophenyl)-6-(4-chlorophenyl)-3-methyl-2-oxopiperidin-1-yl)butanoate

Produkt 1

HCID 585735702-((3S,5R,6S)-3-allyl-5-(3-chlorophenyl)-6-(4-chlorophenyl)-3-methyl-2-oxopiperidin-1-yl)butanoic acid

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a stirred solution of methyl 2-((3S,5R,6S)-3-allyl-5-(3-chlorophenyl)-6-(4-chlorophenyl)-3-methyl-2-oxopiperidin-1-yl)butanoate (200 mg, 0.42 mmol; Example 91, Step A) in THF (5 mL) was added sodium hydroxide (506 mg, 12.65 mmol) in water (5 mL) and the reaction was heated at reflux for about 12 h. After this time the reaction was cooled to rt and partitioned between EtOAc (80 mL) and 1.0 M HCl (20 mL). The separated aqueous layer was extracted with EtOAc (30 mL) and the combined organic layers were dried over MgSO4, filtered and the filtrate was evaporated in vacuo to give the title compound as a white solid. Mass Spectrum (ESI) m/z=460.0 (M+1).

Aufarbeitung

  1. temperaturethe reaction was heated
  2. temperatureat reflux for about 12 h
  3. custompartitioned between EtOAc (80 mL) and 1.0 M HCl (20 mL)
  4. extractionThe separated aqueous layer was extracted with EtOAc (30 mL)
  5. dry with materialthe combined organic layers were dried over MgSO4
  6. filtrationfiltered
  7. customthe filtrate was evaporated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-ef0bbf12464b4c77a256e115c1527def
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08569341B2

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