Hydroxide → HCID 58355545, 화합물

HRID 1184278노트

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HRID 1184278 반응식
[C:1]([O:5][C:6]([N:8]1[CH2:13][C@@H:12]([N:14]([C:19]([C:21]2[N:22]=[N:23][N:24]([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)[C:25]=2[CH2:26][CH2:27][CH2:28][CH2:29][O:30][CH3:31])=O)[CH2:15][CH:16]([CH3:18])[CH3:17])[CH2:11][C@@H:10](C(O)=O)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C1(P([N:55]=[N+]=[N-])(C2C=CC=CC=2)=O)C=CC=CC=1.[Na].[OH-:59]>C1(C)C=CC=CC=1.C(=O)([O-])O.[Na+].C(N(CC)CC)C>[NH2:55][C@@H:10]1[CH2:11][C@H:12]([N:14]([C:19]([C:21]2[N:22]=[N:23][N:24]([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)[C:25]=2[CH2:26][CH2:27][CH2:28][CH2:29][O:30][CH3:31])=[O:59])[CH2:15][CH:16]([CH3:18])[CH3:17])[CH2:13][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[CH2:9]1

참가 물질

8

반응물 4

HCID 961HydroxideHCID 199401P,P-Diphenylphosphinic azideHCID 5360545SodiumHCID 58355160HCID 58355160, 화합물

생성물 1

HCID 58355545HCID 58355545, 화합물

시약·촉매·용매 3

HCID 1140Toluene용매HCID 8471Triethylamine용매HCID 516892Sodium Bicarbonate용매

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온도
100 °C

실험 절차

(3R,5S)-1-(tert-Butoxycarbonyl)-5-[{[5-(4-methoxybutyl)-1-phenyl-1H-1,2,3-triazol-4-yl]carbonyl}(2-methylpropyl)amino]piperidine-3-carboxylic acid (250 mg) was dissolved in toluene (5 ml), diphenylphosphoryl azide (0.15 ml) and triethylamine (94 μl) were added and the mixture was stirred at 100° C. for 2 hr. The reaction mixture was cooled to room temperature, 8M aqueous sodium, hydroxide solution (0.56 ml) was added and the mixture was stirred at room temperature for 1 hr. The reaction mixture was diluted with saturated aqueous sodium hydrogen carbonate and the mixture was extracted twice with ethyl acetate. The extract was dried over anhydrous sodium sulfate and 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 (1:1-1:0) and ethyl acetate-methanol (10:1) was concentrated under reduced pressure to give the object product (155 mg).

후처리

  1. temperatureThe reaction mixture was cooled to room temperature
  2. stirringthe mixture was stirred at room temperature for 1 hr
  3. extractionthe mixture was extracted twice with ethyl acetate
  4. dry with materialThe extract was dried over anhydrous sodium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. washa fraction eluted with ethyl acetate-hexane (1:1-1:0) and ethyl acetate-methanol (10:1)
  7. concentrationwas concentrated under reduced pressure

출처 및 근거

ORD 기록
ord-df26c3e4d383439b96b7e5a417e0a4d8
출처 데이터셋
uspto-grants-2014_03
특허 번호
US08664380B2

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