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

반응식

HRID 2246243 반응식
[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]

참가 물질

5

반응물 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]benzenecarboximidamide2회

생성물 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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-daba1b9e1a96455395463ac052d1e63c
출처 데이터셋
uspto-grants-2010_03
특허 번호
US07687492B2

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