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 2172997노트

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HRID 2172997 반응식
[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]

참가 물질

6

반응물 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

생성물 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-dicarboxylate수율 100%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 57417360Sodium chloride; water용매

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온도
80 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-e7dcbeab7bf1470882595232f03fb5f6
출처 데이터셋
uspto-grants-2015_06
특허 번호
US09056844B2

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