Ammonium Chloride → HCID 57827321, compound

HRID 1842247Notes

Reaction equation

HRID 1842247 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[CH2:22][C@@H:21]([O:23][CH3:24])[CH2:20][CH2:19][C@H:18]1[CH2:17][S:16][C:15]([NH:25][C:26](=[O:32])[O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[N:14]2>[Fe].C(O)C>[NH2:10][C:7]1[CH:8]=[CH:9][C:4]([F:3])=[C:5]([C@:13]23[CH2:22][C@@H:21]([O:23][CH3:24])[CH2:20][CH2:19][C@H:18]2[CH2:17][S:16][C:15]([NH:25][C:26](=[O:32])[O:27][C:28]([CH3:29])([CH3:30])[CH3:31])=[N:14]3)[CH:6]=1

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 57827199HCID 57827199, compound

Product 1

HCID 57827321HCID 57827321, compound

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent

Procedure

Ethanol (5 mL), a saturated ammonium chloride solution (0.5 mL) and iron powder (175 mg) were added to tert-butyl (±)-[(4aR*,7S*,8aS*)-8a-(2-fluoro-5-nitrophenyl)-7-methoxy-4a,5,6,7,8,8a-hexahydro-4H-benzo[d][1,3]thiazin-2-yl]carbamate obtained in Preparation Example 57-(9) (138 mg), and the mixture was stirred with heating under reflux for 30 minutes. The reaction solution was cooled to room temperature, and then the solid was removed by filtration through celite. The filtrate was concentrated under reduced pressure. Then, the residue was suspended in dichloromethane, and the solid was removed by filtration. The filtrate was concentrated under reduced pressure and then purified by silica gel column chromatography to obtain the title compound (98 mg).

Workup

  1. temperaturewith heating
  2. temperatureunder reflux for 30 minutes
  3. customthe solid was removed by filtration through celite
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. customthe solid was removed by filtration
  6. concentrationThe filtrate was concentrated under reduced pressure
  7. custompurified by silica gel column chromatography

Sources & evidence

ORD record
ord-4da0595e87834cc8b09574b2ad04d562
Source dataset
uspto-grants-2015_02
Patent number
US08946210B2

Reaction notes

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