1,3-Bis(diphenylphosphino)propane → Methyl 2-acetylamino-3-(4-amino-3-chloro-5-methyl-phenyl)-propionate

HRID 2116687Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2116687
[C:1]([NH:4]/[C:5](=[CH:10]/[C:11]1[CH:16]=[C:15]([CH3:17])[C:14]([NH2:18])=[C:13]([Cl:19])[CH:12]=1)/[C:6]([O:8][CH3:9])=[O:7])(=[O:3])[CH3:2].C1(P(C2C=CC=CC=2)CCCP(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1CC=CCCC=C1.C1CC=CCCC=C1.[Cl-].[Cl-].[Rh].[Rh]>[C:1]([NH:4][CH:5]([CH2:10][C:11]1[CH:16]=[C:15]([CH3:17])[C:14]([NH2:18])=[C:13]([Cl:19])[CH:12]=1)[C:6]([O:8][CH3:9])=[O:7])(=[O:3])[CH3:2]

Komponenten

4

Edukt 2

HCID 812191,3-Bis(diphenylphosphino)propaneHCID 69363659methyl (E)-2-acetylamino-3-(4-amino-3-chloro-5-methyl-phenyl)-acrylate

Produkt 1

HCID 69196550Methyl 2-acetylamino-3-(4-amino-3-chloro-5-methyl-phenyl)-propionate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6436379Rhodium, di-mu-chlorobis((1,2,5,6-eta)-1,5-cyclooctadiene)di-Katalysator

Versuchsvorschrift

20.6 g (73.0 mmol) methyl (E)-2-acetylamino-3-(4-amino-3-chloro-5-methyl-phenyl)-acrylate, 0.445 g (0.90 mmol) bis(1,5-cyclooctadiene)-di-rhodium(I)-dichloride, 0.744 g (1.8 mmol) 1,3-bis(diphenylphosphino)-propane were dissolved in 400 ml degassed methanol and 12 ml degassed triethylamine and then hydrogenated at ambient temperature under 3 bar hydrogen pressure. The reaction mixture was evaporated down under reduced pressure and taken up in ethyl acetate. The insoluble precipitate was removed by suction filtering and the filtrate was evaporated down under reduced pressure. The residue was purified by column chromatography.

Aufarbeitung

  1. customdegassed methanol and 12 ml
  2. customdegassed triethylamine
  3. customhydrogenated at ambient temperature under 3 bar hydrogen pressure
  4. customThe reaction mixture was evaporated down under reduced pressure
  5. customThe insoluble precipitate was removed by suction
  6. filtrationfiltering
  7. customthe filtrate was evaporated down under reduced pressure
  8. customThe residue was purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-1c5deb9ea85e4555925309a503e43c1b
Quelldatensatz
uspto-grants-2008_10
Patentnummer
US07439237B2

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