Triphenylphosphine → Benzyl (3R)-3-t-butoxycarbonylamino-4-(5-cyano-2-iodophenoxy)butanoate

HRID 747766Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 747766
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:21][OH:22])[CH2:10][C:11]([O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:12])=[O:7])([CH3:4])([CH3:3])[CH3:2].O[C:24]1[CH:25]=[C:26]([CH:29]=[CH:30][C:31]=1[I:32])[C:27]#[N:28].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1(C)C=CC=CC=1>[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:21][O:22][C:24]1[CH:25]=[C:26]([C:27]#[N:28])[CH:29]=[CH:30][C:31]=1[I:32])[CH2:10][C:11]([O:13][CH2:14][C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)=[O:12])=[O:7])([CH3:3])([CH3:4])[CH3:2]

Komponenten

5

Edukt 3

HCID 11776TriphenylphosphineHCID 109446813-Hydroxy-4-iodobenzonitrileHCID 11045079Boc-D-aspartinol 4-Benzyl Ester

Produkt 1

HCID 11731204Benzyl (3R)-3-t-butoxycarbonylamino-4-(5-cyano-2-iodophenoxy)butanoate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

10.16 g (32.8 mmol) of benzyl (3R)-3-t-butoxycarbonylamino-4-hydroxybutanoate was dissolved in 100 ml of toluene. 10.5 g (42.7 mmol) of 3-hydroxy-4-iodobenzonitrile, 11.2 g (42.7 mmol) of triphenylphosphine and 7.4 g (42.7 mmol) of N,N,N′,N′-tetramethylazodicarboxyamide were added to the solution under cooling with ice, and they were stirred at room temperature overnight. The solvent was distilled off, and the residue was purified by the silica gel column chromatography (volume ratio of hexane:ethyl acetate=2:1) to obtain the title compound.

Aufarbeitung

  1. temperatureunder cooling with ice, and they
  2. distillationThe solvent was distilled off
  3. customthe residue was purified by the silica gel column chromatography (volume ratio of hexane:ethyl acetate=2:1)

Quellen und Nachweise

ORD-Eintrag
ord-c96a0ee7ceb94609808e70aa637b32a8
Quelldatensatz
uspto-grants-2008_07
Patentnummer
US07396844B1

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