HCID 131726195, compound → tert-butyl(1S)-1-[3-(2-amino-5-chlorophenoxy)phenyl]ethylcarbamate

HRID 1373243Notes

Reaction equation

HRID 1373243 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N+:25]([O-])=O)=[C:6]([CH:24]=1)[O:7][C:8]1[CH:9]=[C:10]([C@@H:14]([NH:16][C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20])[CH3:15])[CH:11]=[CH:12][CH:13]=1>[C].[Pd].C(OCC)(=O)C>[NH2:25][C:5]1[CH:4]=[CH:3][C:2]([Cl:1])=[CH:24][C:6]=1[O:7][C:8]1[CH:9]=[C:10]([C@@H:14]([NH:16][C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20])[CH3:15])[CH:11]=[CH:12][CH:13]=1

Participants

4

Reactant 1

HCID 131726195HCID 131726195, compound

Product 1

HCID 131726196tert-butyl(1S)-1-[3-(2-amino-5-chlorophenoxy)phenyl]ethylcarbamateYield 99.1%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 8857Ethyl AcetateSolvent

Procedure

5% carbon-palladium (1.1 g) was added to an ethyl acetate (50 ml) solution of tert-butyl(1S)-(-)-1-[3-(5-chloro-2-nitrophenoxy)phenyl]ethylcarbamate (3.5 g, 8.9 mmols). The resulting mixture was hydrogenated at room temperature under atmospheric pressure for 1 hour. The catalyst was removed through filtration, and the filtrate was concentrated under reduced pressure. The residue was purified through silica gel column chromatography to give an oil of tert-butyl(1S)-1-[3-(2-amino-5-chlorophenoxy)phenyl]ethylcarbamate (3.2 g, 99%).

Workup

  1. customThe catalyst was removed through filtration
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe residue was purified through silica gel column chromatography

Sources & evidence

ORD record
ord-71ce2f0581874f33bc43c532f09329aa
Source dataset
uspto-grants-2007_01
Patent number
US07160887B1

Reaction notes

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