Triethylamine → methyl [(2S,4EZ)-1-(biphenyl-4-yl-carbonyl)--4-(methoxyimino)pyrrolidin-2-yl]acetate

HRID 225964

Reaktionsgleichung

Reaktionsgleichung von HRID 225964
[C:1]1([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:6]=[CH:5][C:4]([C:7]([N:9]2[CH2:13][C:12](=O)[CH2:11][C@H:10]2[CH2:15][C:16]([O:18][CH3:19])=[O:17])=[O:8])=[CH:3][CH:2]=1.[CH3:26][O:27][NH3+:28].[Cl-].C(N(CC)CC)C>C(Cl)(Cl)Cl.ClCCl>[C:1]1([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:6]=[CH:5][C:4]([C:7]([N:9]2[CH2:13][C:12](=[N:28][O:27][CH3:26])[CH2:11][C@H:10]2[CH2:15][C:16]([O:18][CH3:19])=[O:17])=[O:8])=[CH:3][CH:2]=1

Komponenten

6

Edukt 3

HCID 8471TriethylamineHCID 11639O-methylhydroxylammonium chlorideHCID 86760911methyl [(2S)-1-(biphenyl-4-ylcarbonyl)-4-oxopyrrolidin-2-yl]acetate

Produkt 1

HCID 131727526methyl [(2S,4EZ)-1-(biphenyl-4-yl-carbonyl)--4-(methoxyimino)pyrrolidin-2-yl]acetateAusbeute 84 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6212ChloroformLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A solution of methyl [(2S)-1-(biphenyl-4-ylcarbonyl)-4-oxopyrrolidin-2-yl]acetate (43 mg, 0.13 mmol), hydroxylamine methyl ether hydrochloride (32 mg, 0.38 mmol) and triethylamine (53 μl, 0.38 mmol) in chloroforme (3 ml) was stirred at 70° C. for 5 days. The reaction mixture was diluted with dichloromethane and washed with HCl 1N. The organic phase was dried (MgSO4) and concentrated to afford methyl [(2S,4EZ)-1-(biphenyl-4-yl-carbonyl)--4-(methoxyimino)pyrrolidin-2-yl]acetate (40 mg). Yield: 62%. HPLC purity: 94%

Aufarbeitung

  1. washwashed with HCl 1N
  2. dry with materialThe organic phase was dried (MgSO4)
  3. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-fd74bb2257964a56a4a9068902b53e9a
Quelldatensatz
uspto-grants-2009_07
Patentnummer
US07557136B2

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