Water → tert-butyl (3S,5R)-3-{[(5,6-difluoro-1H-benzimidazol-2-yl)carbonyl](2-methylpropyl)amino}-5-(morpholin-4-ylcarbonyl)piperidine-1-carboxylate

HRID 1184104ノート

反応式

HRID 1184104 の反応式
[F:1][C:2]1[C:14]([F:15])=[CH:13][C:5]2[NH:6][C:7]([C:9](Cl)(Cl)Cl)=[N:8][C:4]=2[CH:3]=1.[CH3:16][CH:17]([CH3:41])[CH2:18][NH:19][C@H:20]1[CH2:25][C@@H:24]([C:26]([N:28]2[CH2:33][CH2:32][O:31][CH2:30][CH2:29]2)=[O:27])[CH2:23][N:22]([C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])[CH2:21]1.C(=O)([O-])[OH:43].[Na+].O>C1COCC1>[F:1][C:2]1[C:14]([F:15])=[CH:13][C:5]2[NH:6][C:7]([C:9]([N:19]([CH2:18][CH:17]([CH3:41])[CH3:16])[C@H:20]3[CH2:25][C@@H:24]([C:26]([N:28]4[CH2:33][CH2:32][O:31][CH2:30][CH2:29]4)=[O:27])[CH2:23][N:22]([C:34]([O:36][C:37]([CH3:39])([CH3:38])[CH3:40])=[O:35])[CH2:21]3)=[O:43])=[N:8][C:4]=2[CH:3]=1

参加物

6

反応物 4

HCID 962WaterHCID 516892Sodium BicarbonateHCID 231319195,6-difluoro-2-(trichloromethyl)-1H-benzimidazoleHCID 59356577tert-Butyl (3S,5R)-3-(isobutylamino)-5-(morpholine-4-carbonyl)piperidine-1-carboxylate

生成物 1

HCID 58355165tert-butyl (3S,5R)-3-{[(5,6-difluoro-1H-benzimidazol-2-yl)carbonyl](2-methylpropyl)amino}-5-(morpholin-4-ylcarbonyl)piperidine-1-carboxylate収率 70.2%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of 5,6-difluoro-2-(trichloromethyl)-1H-benzimidazole (500 mg) and tert-butyl (3S,5R)-3-[(2-methylpropyl)amino]-5-(morpholin-4-ylcarbonyl)piperidine-1-carboxylate (680 mg) in THF (50 ml) were added sodium hydrogen carbonate (1.3 g) and water (20 ml), and the mixture was stirred at room temperature for 1 hr and extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. The residue was subjected to silica gel column chromatography, and a fraction eluted with ethyl acetate-hexane (1:1-1:0) was concentrated under reduced pressure to give the object product (710 mg).

後処理

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

出典と根拠

ORDレコード
ord-26bc940e3c4a40e68aa076f8ac5c041b
出典データセット
uspto-grants-2014_03
特許番号
US08664380B2

反応ノート

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