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

HRID 567431

反応式

HRID 567431 の反応式
[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>CN(C)C=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]

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 6228Dimethylformamide溶媒

実験手順

3.49 g of naltrexone hydrochloride was suspended in 10.5 ml of N,N-dimethylformamide. 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%).

後処理

  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

出典と根拠

ORDレコード
ord-62f86fc05582497fb1f41dc0b98fd041
出典データセット
uspto-grants-2001_01
特許番号
US06177438B1

関連ノート

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