Ammonium Chloride → Tert-butyl-4-(4-(((4-amino-2-chloro-5-methoxyphenethyl)(tert-butoxycarbonyl)amino)methyl)phenyl)piperazine-1-carboxylate

HRID 1019780Notes

Reaction equation

HRID 1019780 reaction equation
[C:1]([O:5][C:6]([N:8]([CH2:23][C:24]1[CH:29]=[CH:28][C:27]([N:30]2[CH2:35][CH2:34][N:33]([C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37])[CH2:32][CH2:31]2)=[CH:26][CH:25]=1)[CH2:9][CH2:10][C:11]1[CH:16]=[C:15]([O:17][CH3:18])[C:14]([N+:19]([O-])=O)=[CH:13][C:12]=1[Cl:22])=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH4+].[Cl-]>CO.[Zn]>[C:39]([O:38][C:36]([N:33]1[CH2:34][CH2:35][N:30]([C:27]2[CH:28]=[CH:29][C:24]([CH2:23][N:8]([CH2:9][CH2:10][C:11]3[CH:16]=[C:15]([O:17][CH3:18])[C:14]([NH2:19])=[CH:13][C:12]=3[Cl:22])[C:6]([O:5][C:1]([CH3:3])([CH3:2])[CH3:4])=[O:7])=[CH:25][CH:26]=2)[CH2:31][CH2:32]1)=[O:37])([CH3:40])([CH3:41])[CH3:42]

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 67469277Tert-butyl 4-(4-((tert-butoxycarbonyl (2-chloro-5-methoxy-4-nitrophenethyl)amino)methyl)phenyl)piperazine-1-carboxylate

Product 1

HCID 67465937Tert-butyl-4-(4-(((4-amino-2-chloro-5-methoxyphenethyl)(tert-butoxycarbonyl)amino)methyl)phenyl)piperazine-1-carboxylateYield 97%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 887MethanolSolvent

Conditions

Temperature
75 °C

Procedure

To a solution of tert-butyl 4-(4-((tert-butoxycarbonyl (2-chloro-5-methoxy-4-nitrophenethyl)amino)methyl)phenyl)piperazine-1-carboxylate (0.480 g, 0.793 mmol) in methanol (15 mL), a saturated solution of NH4Cl (10 mL) and zinc powder (0.257 g, 3.96 mmol) were added at room temperature and the reaction stirred at 70-80° C. for 1 hour. The mixture was allowed to cool to room temperature and filtered through a celite pad. Water (40 mL) was added to the filtrate and the mixture extracted with EtOAc (2×30 mL). The combined organic extracts were washed with brine (10 mL), dried (Na2SO4) and concentrated under reduced pressure to give the title compound (0.440 g, 97%).

Workup

  1. temperatureto cool to room temperature
  2. filtrationfiltered through a celite pad
  3. additionWater (40 mL) was added to the filtrate
  4. extractionthe mixture extracted with EtOAc (2×30 mL)
  5. washThe combined organic extracts were washed with brine (10 mL)
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-dfdb481ee2cd495399b48b90ab66739f
Source dataset
uspto-grants-2014_05
Patent number
US08716287B2

Reaction notes

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