Water → tert-butyl (3S,5R)-3-[(1H-benzimidazol-2-ylcarbonyl)(propyl)amino]-5-(morpholin-4-ylcarbonyl)piperidine-1-carboxylate

HRID 1260114ノート

反応式

HRID 1260114 の反応式
Cl[C:2](Cl)(Cl)[C:3]1[NH:7][C:6]2[CH:8]=[CH:9][CH:10]=[CH:11][C:5]=2[N:4]=1.[N:14]1([C:20]([C@@H:22]2[CH2:27][C@H:26]([NH:28][CH2:29][CH2:30][CH3:31])[CH2:25][N:24]([C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[CH2:23]2)=[O:21])[CH2:19][CH2:18][O:17][CH2:16][CH2:15]1.[OH2:39]>C1COCC1.C(=O)(O)[O-].[Na+]>[NH:4]1[C:5]2[CH:11]=[CH:10][CH:9]=[CH:8][C:6]=2[N:7]=[C:3]1[C:2]([N:28]([CH2:29][CH2:30][CH3:31])[C@H:26]1[CH2:27][C@@H:22]([C:20]([N:14]2[CH2:19][CH2:18][O:17][CH2:16][CH2:15]2)=[O:21])[CH2:23][N:24]([C:32]([O:34][C:35]([CH3:37])([CH3:36])[CH3:38])=[O:33])[CH2:25]1)=[O:39]

参加物

6

反応物 3

HCID 962WaterHCID 77133Benzimidazole, 2-trichloromethyl-HCID 58355640tert-butyl (3R,5S)-3-(morpholin-4-ylcarbonyl)-5-(propylamino)piperidine-1-carboxylate

生成物 1

HCID 58355218tert-butyl (3S,5R)-3-[(1H-benzimidazol-2-ylcarbonyl)(propyl)amino]-5-(morpholin-4-ylcarbonyl)piperidine-1-carboxylate

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 516892Sodium Bicarbonate溶媒2 回

実験手順

2-(Trichloromethyl)-1H-benzimidazole (1.09 g) and tert-butyl (3R,5S)-3-(morpholin-4-ylcarbonyl)-5-(propylamino)piperidine-1-carboxylate (1.49 g) were dissolved in THF (120 ml), sodium hydrogen carbonate (3.52 g) and water (60 ml) were added and the mixture was stirred at room temperature for 2 hr. The reaction mixture was diluted with aqueous sodium bicarbonate, and extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The residue was subjected to basic silica gel column chromatography, and a fraction eluted with ethyl acetate-hexane (2:8-10:0) was concentrated under reduced pressure to give the object product (1.97 g).

後処理

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. washa fraction eluted with ethyl acetate-hexane (2:8-10:0)
  6. concentrationwas concentrated under reduced pressure

出典と根拠

ORDレコード
ord-1af8277b28f8452eae9a921793f3e997
出典データセット
uspto-grants-2013_06
特許番号
US08466282B2

反応ノート

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