Ammonium Chloride → tert-butyl (+/-)-[(4aR*,8aS*)-8a-(6-amino-2,2-difluorobenzo[1,3]dioxol-4-yl)-4,4a,5,6,8,8a-hexahydro-7-oxa-3-thia-1-azanaphthalen-2-yl]carbamate

HRID 218005

反応式

HRID 218005 の反応式
[Cl-].[NH4+].[F:3][C:4]1([F:34])[O:8][C:7]2[CH:9]=[C:10]([N+:31]([O-])=O)[CH:11]=[C:12]([C@@:13]34[N:22]=[C:21]([NH:23][C:24](=[O:30])[O:25][C:26]([CH3:29])([CH3:28])[CH3:27])[S:20][CH2:19][C@@H:18]3[CH2:17][CH2:16][O:15][CH2:14]4)[C:6]=2[O:5]1>C(O)C.[Fe]>[NH2:31][C:10]1[CH:11]=[C:12]([C@@:13]23[N:22]=[C:21]([NH:23][C:24](=[O:30])[O:25][C:26]([CH3:28])([CH3:27])[CH3:29])[S:20][CH2:19][C@@H:18]2[CH2:17][CH2:16][O:15][CH2:14]3)[C:6]2[O:5][C:4]([F:3])([F:34])[O:8][C:7]=2[CH:9]=1

参加物

5

反応物 2

HCID 25517Ammonium ChlorideHCID 59281222tert-butyl (+/-)-[(4aR*,8aS*)-8a-(2,2-difluoro-6-nitrobenzo[1,3]dioxol-4-yl)-4,4a,5,6,8,8a-hexahydro-7-oxa-3-thia-1-azanaphthalen-2-yl]carbamate

生成物 1

HCID 59281180tert-butyl (+/-)-[(4aR*,8aS*)-8a-(6-amino-2,2-difluorobenzo[1,3]dioxol-4-yl)-4,4a,5,6,8,8a-hexahydro-7-oxa-3-thia-1-azanaphthalen-2-yl]carbamate収率 89%

試薬・触媒・溶媒 2

HCID 23925Iron触媒HCID 702Ethanol溶媒

実験手順

Iron powder (7.09 mg) and a saturated ammonium chloride solution (1.0 ml) were added to a solution of tert-butyl (±)-[(4aR*,8aS*)-8a-(2,2-difluoro-6-nitrobenzo[1,3]dioxol-4-yl)-4,4a,5,6,8,8a-hexahydro-7-oxa-3-thia-1-azanaphthalen-2-yl]carbamate (60.0 mg) in ethanol (20 ml), and the mixture was heated under reflux for 30 minutes. The reaction solution was returned to room temperature and the insoluble matter was removed by filtration through celite. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography to obtain the title compound (50.0 mg).

後処理

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 30 minutes
  3. customwas returned to room temperature
  4. customthe insoluble matter was removed by filtration through celite
  5. customThe solvent was evaporated under reduced pressure
  6. customthe residue was purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-20c13fc941d848969a7f0d203b87fff9
出典データセット
uspto-grants-2012_06
特許番号
US08198269B2

関連ノート

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