Ammonium Chloride → HCID 59281186, compound

HRID 217993Notes

Reaction equation

HRID 217993 reaction equation
[Cl-].[NH4+].[F:3][C:4]1[CH:9]=[CH:8][C:7]([N+:10]([O-])=O)=[CH:6][C:5]=1[C@@:13]12[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]1[CH2:17][C@H:16]([CH2:31][OH:32])[O:15][CH2:14]2>C(O)C.[Fe]>[NH2:10][C:7]1[CH:8]=[CH:9][C:4]([F:3])=[C:5]([C@@:13]23[N:22]=[C:21]([NH:23][C:24](=[O:30])[O:25][C:26]([CH3:28])([CH3:29])[CH3:27])[S:20][CH2:19][C@@H:18]2[CH2:17][C@H:16]([CH2:31][OH:32])[O:15][CH2:14]3)[CH:6]=1

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 59281190HCID 59281190, compound

Product 1

HCID 59281186HCID 59281186, compoundYield 59.9%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent

Procedure

Iron powder (121 mg) and a saturated ammonium chloride solution (1 ml) were added to a solution of tert-butyl [(4aR,6R,8aS)-8a-(2-fluoro-5-nitrophenyl)-6-hydroxymethyl-4,4a,5,6,8,8a-hexahydro-7-oxa-3-thia-1-azanaphthalen-2-yl]carbamate (120 mg) in ethanol (20 ml). The reaction solution was heated under reflux for 40 minutes and then cooled to room temperature. The insoluble matter was filtered off through celite, and the filtrate was evaporated under reduced pressure. The residue was purified by NH-silica gel column chromatography to obtain the title compound (67 mg).

Workup

  1. temperatureThe reaction solution was heated
  2. temperatureunder reflux for 40 minutes
  3. filtrationThe insoluble matter was filtered off through celite
  4. customthe filtrate was evaporated under reduced pressure
  5. customThe residue was purified by NH-silica gel column chromatography

Sources & evidence

ORD record
ord-789a8ca9c59e426d9f910963201502ee
Source dataset
uspto-grants-2012_06
Patent number
US08198269B2

Reaction notes

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