Ammonium Chloride → HCID 67468901, compound

HRID 1019746Notes

Reaction equation

HRID 1019746 reaction equation
[Cl:1][C:2]1[CH:25]=[C:24]([N+:26]([O-])=O)[C:23]([O:29][CH3:30])=[CH:22][C:3]=1[CH2:4][CH2:5][N:6]([CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([F:21])[CH:16]=1)[C:7](=[O:13])[O:8][C:9]([CH3:12])([CH3:11])[CH3:10].[NH4+].[Cl-]>CO.[Zn]>[NH2:26][C:24]1[C:23]([O:29][CH3:30])=[CH:22][C:3]([CH2:4][CH2:5][N:6]([CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([F:21])[CH:16]=2)[C:7](=[O:13])[O:8][C:9]([CH3:12])([CH3:10])[CH3:11])=[C:2]([Cl:1])[CH:25]=1

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 67469272HCID 67469272, compound

Product 1

HCID 67468901HCID 67468901, compoundYield 74%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 887MethanolSolvent

Conditions

Temperature
45 °C

Procedure

To a solution of tert-butyl 2-chloro-5-methoxy-4-nitrophenethyl(3-fluorobenzyl)-carbamate (0.7 g, 1.59 mmol) in methanol (30 mL), saturated solution of NH4Cl (30 mL) was added followed by zinc powder (0.52 g, 7.98 mmol) and the mixture heated to 45° C. for 1.0 h. The mixture was allowed to cool to room temperature, filtered through celite then partitioned between EtOAc (25 mL) and water (50 mL). The separated aqueous phase was extracted with EtOAc (50 mL), then the combined organic extracts were washed with water (50 mL), brine (50 mL), dried (Na2SO4) and concentrated under reduced pressure to give the title compound (0.48 g, 74%).

Workup

  1. temperatureto cool to room temperature
  2. filtrationfiltered through celite
  3. customthen partitioned between EtOAc (25 mL) and water (50 mL)
  4. extractionThe separated aqueous phase was extracted with EtOAc (50 mL)
  5. washthe combined organic extracts were washed with water (50 mL), brine (50 mL)
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-314c93b1c2324ae0a428dfcffef4ae73
Source dataset
uspto-grants-2014_05
Patent number
US08716287B2

Reaction notes

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