Sodium Azide → (+/-)-N,N-di(tert-butyloxycarbonyl)-[(4aR*,8aR*)-8a-(4-azidothiophen-2-yl)-4,4a,5,6,8,8a-hexahydro-7-oxa-3-thia-1-azanaphthalen-2-yl]amine

HRID 218000ノート

反応式

HRID 218000 の反応式
[N-:1]=[N+:2]=[N-:3].[Na+].[C:5]([O:9][C:10]([N:12]([C:20]1[S:29][CH2:28][C@H:27]2[C@:22]([C:30]3[S:31][CH:32]=[C:33](B4OC(C)(C)C(C)(C)O4)[CH:34]=3)([CH2:23][O:24][CH2:25][CH2:26]2)[N:21]=1)[C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])=[O:11])([CH3:8])([CH3:7])[CH3:6]>CO.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[C:5]([O:9][C:10]([N:12]([C:20]1[S:29][CH2:28][C@H:27]2[C@:22]([C:30]3[S:31][CH:32]=[C:33]([N:1]=[N+:2]=[N-:3])[CH:34]=3)([CH2:23][O:24][CH2:25][CH2:26]2)[N:21]=1)[C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])=[O:11])([CH3:6])([CH3:7])[CH3:8]

参加物

5

反応物 2

HCID 33557Sodium AzideHCID 58406029(+/-)-N,N-di(tert-butyloxycarbonyl)-[(4aR*,8aR*)-8a-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-thiophen-2-yl]-4,4a,5,6,8,8a-hexahydro-7-oxa-3-thia-1-azanaphthalen-2-yl]amine

生成物 1

HCID 58406041(+/-)-N,N-di(tert-butyloxycarbonyl)-[(4aR*,8aR*)-8a-(4-azidothiophen-2-yl)-4,4a,5,6,8,8a-hexahydro-7-oxa-3-thia-1-azanaphthalen-2-yl]amine収率 74.6%

試薬・触媒・溶媒 2

HCID 8895Cupric acetate触媒HCID 887Methanol溶媒

実験手順

Sodium azide (177 mg) and copper (II) acetate (99.2 mg) were added to a solution of (±)-N,N-di(tert-butyloxycarbonyl)-[(4aR*,8aR*)-8a-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-thiophen-2-yl]-4,4a,5,6,8,8a-hexahydro-7-oxa-3-thia-1-azanaphthalen-2-yl]amine (790 mg) in methanol (88 ml). The mixture was stirred at room temperature overnight, and then the excess of methanol was evaporated under reduced pressure. An ammonium chloride solution was added to the residue, and the aqueous layer was with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by NH-silica gel column chromatography to obtain the title compound (503 mg).

後処理

  1. customthe excess of methanol was evaporated under reduced pressure
  2. additionAn ammonium chloride solution was added to the residue
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by NH-silica gel column chromatography

出典と根拠

ORDレコード
ord-e5096ae6d217401ab14988f28bf335a2
出典データセット
uspto-grants-2012_06
特許番号
US08198269B2

反応ノート

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