Imidazole → 3-Tert-butyldimethylsilyloxy-17-cyclopropylmethyl-4,5alpha-epoxy-14beta-hydroxy-6-oxomorphinan

HRID 430704

반응식

HRID 430704 반응식
[CH:1]1[C:6]2[CH2:7][C@H:8]3[N:13]([CH2:14][CH:15]4[CH2:17][CH2:16]4)[CH2:12][CH2:11][C@:10]45[C@H:18]([C:20]([CH2:22][CH2:23][C@@:9]34[OH:24])=[O:21])[O:19][C:4]([C:5]=25)=[C:3]([OH:25])[CH:2]=1.Cl.N1C=CN=C1.[C:32]([Si:36]([CH3:39])([CH3:38])Cl)([CH3:35])([CH3:34])[CH3:33].O>C(OCC)C>[Si:36]([O:25][C:3]1[CH:2]=[CH:1][C:6]2[CH2:7][C@H:8]3[N:13]([CH2:14][CH:15]4[CH2:17][CH2:16]4)[CH2:12][CH2:11][C@:10]45[C:5]=2[C:4]=1[O:19][C@H:18]4[C:20](=[O:21])[CH2:22][CH2:23][C@@:9]35[OH:24])([C:32]([CH3:35])([CH3:34])[CH3:33])([CH3:39])[CH3:38]

참가 물질

6

반응물 4

HCID 795ImidazoleHCID 962WaterHCID 28928tert-Butyldimethylsilyl chlorideHCID 5485201Naltrexone Hydrochloride

생성물 1

HCID 143947793-Tert-butyldimethylsilyloxy-17-cyclopropylmethyl-4,5alpha-epoxy-14beta-hydroxy-6-oxomorphinan수율 76%

시약·촉매·용매 1

HCID 3283Diethyl Ether용매

실험 절차

3.49 g of naltrexone hydrochloride was suspended in 10.5 ml of N,N-dimethylfonnamde. After adding 3.46 g of imidazole, 3.48 g of tert-butyldimethylchlorosilane was added followed by stirring for 35 minutes at room temperature. 30 ml of water and 50 ml of diethyl ether were added to the reaction system followed by separation. The aqueous layer was extracted twice with 30 ml of diethyl ether. The combined extracts were dried over anhydrous sodium sulfate and concentrated. The resulting residue was recrystallized from ethanol to obtain 3.2 g of the target compound (yield: 76%).

후처리

  1. additionwas added
  2. customfollowed by separation
  3. extractionThe aqueous layer was extracted twice with 30 ml of diethyl ether
  4. dry with materialThe combined extracts were dried over anhydrous sodium sulfate
  5. concentrationconcentrated
  6. customThe resulting residue was recrystallized from ethanol

출처 및 근거

ORD 기록
ord-729b126d6f8d4bf79da0b2f86e57e8d0
출처 데이터셋
uspto-grants-2001_11
특허 번호
US06323212B1

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