1,1'-Carbonyldiimidazole → 1-[(2S,3S)-2-[(tert-Butoxycarbonyl)amino]-3-[3-[2-chloro-4-[(methylsulfonyl)amino]phenyl]-1,2,4-oxadiazol-5-yl]-1-oxobutyl]pyrrolidine

HRID 2246243

Reaktionsgleichung

Reaktionsgleichung von HRID 2246243
[C:1]([O:5][C:6]([NH:8][C@H:9]([C:15](=[O:21])[N:16]1[CH2:20][CH2:19][CH2:18][CH2:17]1)[C@H:10]([CH3:14])[C:11]([OH:13])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N1C=CN=C1)(N1C=CN=C1)=O.[Cl:34][C:35]1[CH:40]=[C:39]([NH:41][S:42]([CH3:45])(=[O:44])=[O:43])[CH:38]=[CH:37][C:36]=1[C:46](=[N:48]O)[NH2:47]>ClCCl>[C:1]([O:5][C:6]([NH:8][C@@H:9]([C@@H:10]([C:11]1[O:13][N:48]=[C:46]([C:36]2[CH:37]=[CH:38][C:39]([NH:41][S:42]([CH3:45])(=[O:44])=[O:43])=[CH:40][C:35]=2[Cl:34])[N:47]=1)[CH3:14])[C:15]([N:16]1[CH2:20][CH2:19][CH2:18][CH2:17]1)=[O:21])=[O:7])([CH3:2])([CH3:3])[CH3:4]

Komponenten

5

Edukt 3

HCID 682631,1'-CarbonyldiimidazoleHCID 68431373(2S,3S)-3-[(tert-Butoxycarbonyl)amino]-2-methyl-4-oxo-4-pyrrolidin-1-ylbutanoic acidHCID 725337992-Chloro-N'-hydroxy-4-[(methylsulfonyl)amino]benzenecarboximidamide2×

Produkt 1

HCID 684290061-[(2S,3S)-2-[(tert-Butoxycarbonyl)amino]-3-[3-[2-chloro-4-[(methylsulfonyl)amino]phenyl]-1,2,4-oxadiazol-5-yl]-1-oxobutyl]pyrrolidine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a stirred solution of the product from Step B (132.0 mg, 0.44 mmol) in dichloromethane (5 mL) was added 1,1′-carbonyldiimidazole (148.0 mg, 0.91 mmol). After stirring at room temperature for 1 h, 2-chloro-N′-hydroxy-4-[(methylsulfonyl)amino]benzenecarboximidamide (Intermediate 6, 145.0 mg, 0.55 mmol) was added. After stirring at room temperature for 2 h, the reaction was quenched with saturated aqueous ammonium chloride solution. The organic phase was then dried over anhydrous sodium sulfate and concentrated in vacuo. The residue was dissolved in 10 mL of toluene and heated at 110° C. for 12 h. The toluene was removed under reduced pressure and the residue was then purified by preparative thin layer chromatography (silica gel, 30:70 hexanes/ethyl acetate) to give the desired product.

Aufarbeitung

  1. stirringAfter stirring at room temperature for 2 h
  2. customthe reaction was quenched with saturated aqueous ammonium chloride solution
  3. dry with materialThe organic phase was then dried over anhydrous sodium sulfate
  4. concentrationconcentrated in vacuo
  5. dissolutionThe residue was dissolved in 10 mL of toluene
  6. temperatureheated at 110° C. for 12 h
  7. customThe toluene was removed under reduced pressure
  8. customthe residue was then purified by preparative thin layer chromatography (silica gel, 30:70 hexanes/ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-daba1b9e1a96455395463ac052d1e63c
Quelldatensatz
uspto-grants-2010_03
Patentnummer
US07687492B2

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