Potassium Carbonate → Di-tert-butyl (1R,2R,3S,4S,5R,6R)-2-(tert-butoxycarbonylamino)-3-[(3,4-dichlorophenyl)methoxy]-4-[(2-methyl-1,2,4-triazol-3-yl)sulfanyl]bicyclo[3.1.0]hexane-2,6-dicarboxylate

HRID 2172997ノート

反応式

HRID 2172997 の反応式
[CH3:1][N:2]1[C:6](=[S:7])[N:5]=[CH:4][NH:3]1.C(=O)([O-])[O-].[K+].[K+].[C:14]([O:18][C:19]([NH:21][C@@:22]1([C:50]([O:52][C:53]([CH3:56])([CH3:55])[CH3:54])=[O:51])[C@H:27]([O:28][CH2:29][C:30]2[CH:35]=[CH:34][C:33]([Cl:36])=[C:32]([Cl:37])[CH:31]=2)[C@H:26](OS(C)(=O)=O)[C@@H:25]2[C@H:23]1[C@H:24]2[C:43]([O:45][C:46]([CH3:49])([CH3:48])[CH3:47])=[O:44])=[O:20])([CH3:17])([CH3:16])[CH3:15]>CN(C)C=O.[Cl-].[Na+].O>[C:14]([O:18][C:19]([NH:21][C@@:22]1([C:50]([O:52][C:53]([CH3:56])([CH3:55])[CH3:54])=[O:51])[C@H:27]([O:28][CH2:29][C:30]2[CH:35]=[CH:34][C:33]([Cl:36])=[C:32]([Cl:37])[CH:31]=2)[C@@H:26]([S:7][C:6]2[N:2]([CH3:1])[N:3]=[CH:4][N:5]=2)[C@@H:25]2[C@H:23]1[C@H:24]2[C:43]([O:45][C:46]([CH3:48])([CH3:47])[CH3:49])=[O:44])=[O:20])([CH3:17])([CH3:15])[CH3:16]

参加物

6

反応物 3

HCID 11430Potassium CarbonateHCID 30381873H-1,2,4-Triazole-3-thione, 1,2-dihydro-2-methyl-HCID 86695975Di-tert-butyl (1S,2R,3S,4R,5R,6R)-2-[(tert-butoxycarbonyl)amino]-3-[(3,4-dichlorobenzyl)oxy]-4-[(methylsulfonyl)oxy]bicyclo[3.1.0]hexane-2,6-dicarboxylate

生成物 1

HCID 67708365Di-tert-butyl (1R,2R,3S,4S,5R,6R)-2-(tert-butoxycarbonylamino)-3-[(3,4-dichlorophenyl)methoxy]-4-[(2-methyl-1,2,4-triazol-3-yl)sulfanyl]bicyclo[3.1.0]hexane-2,6-dicarboxylate収率 100%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 57417360Sodium chloride; water溶媒

反応条件

温度
80 °C

実験手順

Add 2-methyl-1H-1,2,4-triazole-3-thione (0.126 g, 1.09 mmol) and potassium carbonate (0.35 g, 2.52 mmol) to a solution of di-tert-butyl (1S,2R,3S,4R,5R,6R)-2-[(tert-butoxycarbonyl)amino]-3-[(3,4-dichlorobenzyl)oxy]-4-[(methylsulfonyl)oxy]bicyclo[3.1.0]hexane-2,6-dicarboxylate (0.80 g, 0.84 mmol) in dimethylformamide (1.68 mL. After heating for 2 days at 80° C., pour the solution into brine and extract with ethyl acetate three times, dry the combined organic phases with sodium sulfate, filter and concentrate under reduced pressure. Purify by flash chromatography eluting with 10% ethyl acetate/CH2Cl2 to yield the title compound as an oil (0.576 g, 0.84 mmol, 100%). MS (m/z): 685/687/689 (M+1).

後処理

  1. extractionextract with ethyl acetate three times
  2. dry with materialdry the combined organic phases with sodium sulfate
  3. filtrationfilter
  4. concentrationconcentrate under reduced pressure
  5. customPurify by flash chromatography
  6. washeluting with 10% ethyl acetate/CH2Cl2

出典と根拠

ORDレコード
ord-e7dcbeab7bf1470882595232f03fb5f6
出典データセット
uspto-grants-2015_06
特許番号
US09056844B2

反応ノート

読み込み中…