(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

反応式

HRID 1630074 の反応式
[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]

参加物

3

反応物 1

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 313Hydrochloric Acid溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-1d8ac74da33947c78a6756ca09ab2d45
出典データセット
uspto-grants-2014_07
特許番号
US08791102B2

関連ノート

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