Ammonium Chloride → HCID 57827202, compound

HRID 1693163Notes

Reaction equation

HRID 1693163 reaction equation
[C:1]([O:5][C:6](=[O:29])[NH:7][C:8]1[S:9][CH2:10][C@@H:11]2[CH2:16][C@H:15]([O:17][CH3:18])[CH2:14][C@:12]2([C:19]2[CH:24]=[C:23]([N+:25]([O-])=O)[CH:22]=[CH:21][C:20]=2[F:28])[N:13]=1)([CH3:4])([CH3:3])[CH3:2].[Cl-].[NH4+].O.C(OCC)(=O)C>C(O)C.[Fe]>[C:1]([O:5][C:6](=[O:29])[NH:7][C:8]1[S:9][CH2:10][C@@H:11]2[CH2:16][C@H:15]([O:17][CH3:18])[CH2:14][C@:12]2([C:19]2[CH:24]=[C:23]([NH2:25])[CH:22]=[CH:21][C:20]=2[F:28])[N:13]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 25517Ammonium ChlorideHCID 22728543Water ethylacetateHCID 57827201HCID 57827201, compound

Product 1

HCID 57827202HCID 57827202, compoundYield 75.7%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent

Procedure

A solution of tert-butyl[(4aR*,6S*,7aS*)-7a-(2-fluoro-5-nitrophenyl)-6-methoxy-4,4a,5,6,7,7a-hexahydrocyclopenta[d][1,3]thiazin-2-yl]carbamate (118 mg) and iron (133 mg) in ethanol (8 mL)—a saturated ammonium chloride solution (0.303 mL) was stirred at 87° C. for 30 minutes. The reaction solution was cooled to room temperature and then poured into water-ethyl acetate, followed by extraction with ethyl acetate. The extract was washed with a saturated sodium chloride solution and then dried over anhydrous magnesium sulfate. The drying agent was removed by filtration and the filtrate was concentrated under reduced pressure. The resulting crude product was purified by silica gel column chromatography to obtain the title compound (83 mg).

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe extract was washed with a saturated sodium chloride solution
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe drying agent was removed by filtration
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customThe resulting crude product was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-6cfa3b969c1d4962a90927e7d9cc7d73
Source dataset
uspto-grants-2012_04
Patent number
US08158620B2

Reaction notes

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