Diisopropylethylamine → 1-tert-butyl 3-methyl (3R,5S)-5-[({1-(2-fluorophenyl)-5-[(methylsulfanyl)methyl]-1H-1,2,3-triazol-4-yl}carbonyl)(2-methylpropyl)amino]piperidine-1,3-dicarboxylate

HRID 1509580노트

반응식

HRID 1509580 반응식
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:12]([CH2:13][S:14][CH3:15])=[C:11]([C:16]([OH:18])=O)[N:10]=[N:9]1.[CH2:19]([NH:23][C@@H:24]1[CH2:29][N:28]([C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[CH2:27][C@H:26]([C:37]([O:39][CH3:40])=[O:38])[CH2:25]1)[CH:20]([CH3:22])[CH3:21].C(N(CC)C(C)C)(C)C.F[P-](F)(F)(F)(F)F.ClC(N(C)C)=[N+](C)C>ClCCCl.C(=O)([O-])O.[Na+]>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:12]([CH2:13][S:14][CH3:15])=[C:11]([C:16]([N:23]([CH2:19][CH:20]([CH3:22])[CH3:21])[C@@H:24]2[CH2:29][N:28]([C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[CH2:27][C@H:26]([C:37]([O:39][CH3:40])=[O:38])[CH2:25]2)=[O:18])[N:10]=[N:9]1

참가 물질

7

반응물 4

HCID 81531DiisopropylethylamineHCID 10989639Chloro-N,N,N',N'-tetramethylformamidinium HexafluorophosphateHCID 58355170HCID 58355170, 화합물HCID 593566071-tert-butyl 3-methyl (3R,5S)-5-[(2-methylpropyl)amino]piperidine-1,3-dicarboxylate

생성물 1

HCID 583554821-tert-butyl 3-methyl (3R,5S)-5-[({1-(2-fluorophenyl)-5-[(methylsulfanyl)methyl]-1H-1,2,3-triazol-4-yl}carbonyl)(2-methylpropyl)amino]piperidine-1,3-dicarboxylate수율 79%

시약·촉매·용매 2

HCID 111,2-Dichloroethane용매HCID 516892Sodium Bicarbonate용매

실험 절차

1-(2-Fluorophenyl)-5-[(methylsulfanyl)methyl]-1H-1,2,3-triazole-4-carboxylic acid (960 mg), 1-tert-butyl 3-methyl (3R,5S)-5-(isobutylamino)piperidine-1,3-dicarboxylate (1.15 g) and N,N-diisopropylethylamine (1.6 μl) were dissolved in 1,2-dichloroethane (10 ml), chloro-N,N,N′,N′-tetramethylformamidinium hexafluorophosphate (1.50 g) was added and the mixture was stirred at room temperature for 3 days. The reaction mixture was diluted with saturated aqueous sodium hydrogen carbonate solution and the mixture was 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 silica gel column chromatography, and a fraction eluted with ethyl acetate-hexane (10:90-100:0) was concentrated under reduced pressure to give the object product (1.60 g).

후처리

  1. extractionthe mixture was extracted 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 (10:90-100:0)
  6. concentrationwas concentrated under reduced pressure

출처 및 근거

ORD 기록
ord-d541248b68e04ef1ba04cb7f95022175
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09221836B2

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