Ethyl Acetate → HCID 69351806, compound

HRID 1373250Notes

Reaction equation

HRID 1373250 reaction equation
C(OCC)(=O)C.[Cl:7][C:8]1[CH:9]=[CH:10][C:11]([N+:31]([O-])=O)=[C:12]([CH:30]=1)[O:13][C:14]1[CH:15]=[C:16]([C@H:20]([NH:22][C:23](=[O:29])[O:24][C:25]([CH3:28])([CH3:27])[CH3:26])[CH3:21])[CH:17]=[CH:18][CH:19]=1.Br[CH2:35][CH2:36][CH2:37][C:38]([O:40][CH2:41][CH3:42])=[O:39].C(=O)([O-])[O-].[K+].[K+]>[C].[Pd].O.CN(C)C=O>[C:25]([O:24][C:23]([NH:22][C@@H:20]([C:16]1[CH:15]=[C:14]([CH:19]=[CH:18][CH:17]=1)[O:13][C:12]1[CH:30]=[C:8]([Cl:7])[CH:9]=[CH:10][C:11]=1[NH:31][CH2:35][CH2:36][CH2:37][C:38]([O:40][CH2:41][CH3:42])=[O:39])[CH3:21])=[O:29])([CH3:28])([CH3:27])[CH3:26]

Participants

8

Reactant 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 76300Ethyl 4-bromobutyrateHCID 131726197HCID 131726197, compound

Product 1

HCID 69351806HCID 69351806, compoundYield 56.5%

Reagents, catalysts & solvents 3

HCID 178418390HCID 178418390, compoundCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

5% carbon-palladium (1.I g) was added to an ethyl acetate (50 ml) solution of tert-butyl(1R)-(-)-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 stirred with ethyl 4-bromobutyrate (7 g, 36 mmols), potassium carbonate (3.7 g, 27 mmols) and N,N-dimethylformamide (50 ml) at 80° C. for 72 hours. The reaction mixture was cooled, poured into water, and extracted with ethyl acetate. The extract was washed with water, and then dried with anhydrous magnesium sulfate. This was concentrated under reduced pressure, and the residue was purified through silica gel column chromatography to give an oil of ethyl 4-[N-[2-[3-[(1R)-1-tert-butoxycarbonylaminoethyl]phenoxy]-4-chlorophenyl]]aminobutyrate (2.4 g, 56%).

Workup

  1. customThe catalyst was removed through filtration
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. temperatureThe reaction mixture was cooled
  4. extractionextracted with ethyl acetate
  5. washThe extract was washed with water
  6. dry with materialdried with anhydrous magnesium sulfate
  7. concentrationThis was concentrated under reduced pressure
  8. customthe residue was purified through silica gel column chromatography

Sources & evidence

ORD record
ord-d65f4c3788ee4c1388b1710593f360ce
Source dataset
uspto-grants-2007_01
Patent number
US07160887B1

Reaction notes

Loading…