Ammonium Chloride → 4-[4-((S)-1-{[2-(4-amino-2-chloro-5-methoxy-phenyl)-ethyl]-tert-butoxycarbonyl-amino}ethyl)-phenyl]piperazine-1-carboxylic acid tert-butyl ester

HRID 1019776Notes

Reaction equation

HRID 1019776 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][C:17]([C@@H:20]([N:22]([C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])[CH2:23][CH2:24][C:25]3[CH:30]=[C:29]([O:31][CH3:32])[C:28]([N+:33]([O-])=O)=[CH:27][C:26]=3[Cl:36])[CH3:21])=[CH:16][CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH4+].[Cl-]>CO.[Zn]>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][C:17]([C@@H:20]([N:22]([CH2:23][CH2:24][C:25]3[CH:30]=[C:29]([O:31][CH3:32])[C:28]([NH2:33])=[CH:27][C:26]=3[Cl:36])[C:37]([O:39][C:40]([CH3:42])([CH3:43])[CH3:41])=[O:38])[CH3:21])=[CH:16][CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 674692684-[4-((S)-1-{tert-butoxycarbonyl-[2-(2-chloro-5-methoxy-4-nitro-phenyl)-ethyl]amino}-ethyl)phenyl]-piperazine-1-carboxylic acid tert-butyl ester

Product 1

HCID 674689714-[4-((S)-1-{[2-(4-amino-2-chloro-5-methoxy-phenyl)-ethyl]-tert-butoxycarbonyl-amino}ethyl)-phenyl]piperazine-1-carboxylic acid tert-butyl esterYield 89.7%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 887MethanolSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 4-[4-((S)-1-{tert-butoxycarbonyl-[2-(2-chloro-5-methoxy-4-nitro-phenyl)-ethyl]amino}-ethyl)phenyl]-piperazine-1-carboxylic acid tert-butyl ester (0.32 g, 0.53 mmol) in methanol (12 mL), a saturated solution of NH4Cl (8 mL) and zinc powder (0.175 g, 2.66 mmol) were added at room temperature and the reaction was stirred at 80° C. for 2 hours. The mixture was allowed to cool to room temperature and then filtered through cotton wool. Water (50 mL) was added and the mixture extracted with EtOAc (2×30 mL). The combined organic extracts were washed with brine (20 mL), dried (Na2SO4) and concentrated under reduced pressure to give the title compound (0.28 g, 89%) which was used without further purification.

Workup

  1. temperatureto cool to room temperature
  2. filtrationfiltered through cotton wool
  3. additionWater (50 mL) was added
  4. extractionthe mixture extracted with EtOAc (2×30 mL)
  5. washThe combined organic extracts were washed with brine (20 mL)
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-ec9807a5e70e40939413169b5e3ea383
Source dataset
uspto-grants-2014_05
Patent number
US08716287B2

Reaction notes

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