Dimethylformamide → ethyl 4-[N-[2-[3-[(1S)-1-tert-butoxycarbonylaminoethyl]phenoxy]-4-chlorophenyl]]aminobutyrate

HRID 1373244Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1373244
[NH2:1][C:2]1[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][C:3]=1[O:4][C:5]1[CH:6]=[C:7]([C@@H:11]([NH:13][C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17])[CH3:12])[CH:8]=[CH:9][CH:10]=1.Br[CH2:27][CH2:28][CH2:29][C:30]([O:32][CH2:33][CH3:34])=[O:31].C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O>[C:16]([O:15][C:14]([NH:13][C@H:11]([C:7]1[CH:6]=[C:5]([CH:10]=[CH:9][CH:8]=1)[O:4][C:3]1[CH:21]=[C:22]([Cl:25])[CH:23]=[CH:24][C:2]=1[NH:1][CH2:27][CH2:28][CH2:29][C:30]([O:32][CH2:33][CH3:34])=[O:31])[CH3:12])=[O:20])([CH3:19])([CH3:18])[CH3:17]

Komponenten

6

Edukt 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 76300Ethyl 4-bromobutyrateHCID 131726196tert-butyl(1S)-1-[3-(2-amino-5-chlorophenoxy)phenyl]ethylcarbamate

Produkt 1

HCID 69353407ethyl 4-[N-[2-[3-[(1S)-1-tert-butoxycarbonylaminoethyl]phenoxy]-4-chlorophenyl]]aminobutyrateAusbeute 66,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A mixture of tert-butyl(1S)-1-[3-(2-amino-5-chlorophenoxy)phenyl]ethylcarbamate (3.2 g, 8.8 mmols), ethyl 4-bromobutyrate (14 g, 70 mmols), potassium carbonate (3.6 g, 26 mmols) and N,N-dimethylformamide (50 ml) was stirred at 80° C. for 48 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-[(1S)-1-tert-butoxycarbonylaminoethyl]phenoxy]-4-chlorophenyl]]aminobutyrate (2.8 g, 66%).

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-fb27c522584d4b29a55cf9e9c3296293
Quelldatensatz
uspto-grants-2007_01
Patentnummer
US07160887B1

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