Trimethylsilyldiazomethane → methyl 3-[(2R,4EZ)-1-(biphenyl-4-ylcarbonyl)-4-(methoxyimino)pyrrolidin-2-yl]propanoate

HRID 225965

Reaktionsgleichung

Reaktionsgleichung von HRID 225965
[C:1]1([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:6]=[CH:5][C:4]([C:7]([N:9]2[CH2:13][C:12](=[N:14][O:15][CH3:16])[CH2:11][C@H:10]2[CH2:17][CH2:18][C:19]([OH:21])=[O:20])=[O:8])=[CH:3][CH:2]=1.[N+](=[CH:30][Si](C)(C)C)=[N-]>C1(C)C(CO)=CC=CC=1>[C:1]1([C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH:2]=[CH:3][C:4]([C:7]([N:9]2[CH2:13][C:12](=[N:14][O:15][CH3:16])[CH2:11][C@H:10]2[CH2:17][CH2:18][C:19]([O:21][CH3:30])=[O:20])=[O:8])=[CH:5][CH:6]=1

Komponenten

4

Edukt 2

HCID 167693TrimethylsilyldiazomethaneHCID 1317275283-[(2R,4EZ)-1-(biphenyl-4-ylcarbonyl)-4-(methoxyimino)pyrrolidin-2-yl]propanoic acid2×

Produkt 1

HCID 131727527methyl 3-[(2R,4EZ)-1-(biphenyl-4-ylcarbonyl)-4-(methoxyimino)pyrrolidin-2-yl]propanoateAusbeute 96 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 69942-Methylbenzyl alcoholLösungsmittel

Versuchsvorschrift

To a solution of 3-[(2R,4EZ)-1-(biphenyl-4-ylcarbonyl)-4-(methoxyimino)pyrrolidin-2-yl]propanoic acid (Intermediate 8, 20 mg, 0.05 mmol) in toluene-methanol (1 ml, 3-1) was added (diazomethyl)trimethylsilane (0.110 ml, 2M in hexane). After 3 hours, the reaction mixture was concentrated and purified by silica gel column chromatography (ethyl acetate) to give methyl 3-[(2R,4EZ)-1-(biphenyl-4-ylcarbonyl)-4-(methoxyimino)pyrrolidin-2-yl]propanoate (20 mg). Yield: 96%. HPLC purity: 94%

Aufarbeitung

  1. concentrationthe reaction mixture was concentrated
  2. custompurified by silica gel column chromatography (ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-9a97026e02ac4b98842f0e341208e0bf
Quelldatensatz
uspto-grants-2009_07
Patentnummer
US07557136B2

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