(2S,4R)-tert-butyl 4-cyano-2-(4-(4-fluorophenoxy)phenylcarbamoyl)pyrrolidine-1-carboxylate → (2S,4R)-4-cyano-N-(4-(4-fluorophenoxy)phenyl)pyrrolidine-2-carboxamide

HRID 1630074

반응식

HRID 1630074 반응식
[C:1]([C@H:3]1[CH2:7][N:6](C(OC(C)(C)C)=O)[C@H:5]([C:15](=[O:31])[NH:16][C:17]2[CH:22]=[CH:21][C:20]([O:23][C:24]3[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=3)=[CH:19][CH:18]=2)[CH2:4]1)#[N:2]>Cl>[C:1]([C@H:3]1[CH2:7][NH:6][C@H:5]([C:15]([NH:16][C:17]2[CH:18]=[CH:19][C:20]([O:23][C:24]3[CH:25]=[CH:26][C:27]([F:30])=[CH:28][CH:29]=3)=[CH:21][CH:22]=2)=[O:31])[CH2:4]1)#[N:2]

참가 물질

3

반응물 1

HCID 67009351(2S,4R)-tert-butyl 4-cyano-2-(4-(4-fluorophenoxy)phenylcarbamoyl)pyrrolidine-1-carboxylate

생성물 1

HCID 67010040(2S,4R)-4-cyano-N-(4-(4-fluorophenoxy)phenyl)pyrrolidine-2-carboxamide수율 65%

시약·촉매·용매 1

HCID 313Hydrochloric Acid용매

실험 절차

The crude (2S,4R)-tert-butyl 4-cyano-2-(4-(4-fluorophenoxy)phenylcarbamoyl)pyrrolidine-1-carboxylate was combined with hydrogen chloride (4N in dioxane, 20 mL). The mixture was stirred at ambient temperature for 1 hour and then quenched with saturated sodium bicarbonate (aq., 100 mL). The mixture was extracted with ethyl acetate (30 mL) and the extract was washed with deionized water (30 mL) and then brine (30 mL), dried over anhydrous sodium sulfate, filtered and concentrated. The residue was triturated with ethyl acetate to give (2S,4R)-4-cyano-N-(4-(4-fluorophenoxy)phenyl)pyrrolidine-2-carboxamide (0.88 g, 2.69 mmol, 65% yield over 2 steps) as an off-white solid.

후처리

  1. customquenched with saturated sodium bicarbonate (aq., 100 mL)
  2. extractionThe mixture was extracted with ethyl acetate (30 mL)
  3. washthe extract was washed with deionized water (30 mL)
  4. dry with materialbrine (30 mL), dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was triturated with ethyl acetate

출처 및 근거

ORD 기록
ord-1d8ac74da33947c78a6756ca09ab2d45
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08791102B2

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