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

Reaction equation

HRID 218005 reaction equation
[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

Participants

5

Reactant 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

Product 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]carbamateYield 89%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-20c13fc941d848969a7f0d203b87fff9
Source dataset
uspto-grants-2012_06
Patent number
US08198269B2

Linked notes

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