Triphenylphosphine → (2S)-2-((tert-butoxycarbonyl)amino)hexane-3-yl 4-nitrobenzoate

HRID 340505Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 340505
[N+:1]([C:4]1[CH:12]=[CH:11][C:7]([C:8]([O-:10])=[O:9])=[CH:6][CH:5]=1)([O-:3])=[O:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O.[C:46]([O:50][C:51](=[O:60])[NH:52][C@H:53]([CH:55](O)[CH2:56][CH2:57][CH3:58])[CH3:54])([CH3:49])([CH3:48])[CH3:47]>O1CCCC1>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([C:8]([O:10][CH:55]([CH2:56][CH2:57][CH3:58])[C@@H:53]([NH:52][C:51]([O:50][C:46]([CH3:49])([CH3:48])[CH3:47])=[O:60])[CH3:54])=[O:9])=[CH:11][CH:12]=1)([O-:3])=[O:2]

Komponenten

6

Edukt 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 44199404-NitrobenzoateHCID 87514848tert-butyl((2S)-3-hydroxyhexan-2-yl)carbamate

Produkt 1

HCID 86683881(2S)-2-((tert-butoxycarbonyl)amino)hexane-3-yl 4-nitrobenzoateAusbeute 59,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

4-nitrobenzoate (16.3 g), triphenylphosphine (32 g), and diisopropyl azodicarboxylate (40% toluene solution) (64 ml) were added dropwise to a tetrahydrofuran (50 ml) solution containing tert-butyl((2S)-3-hydroxyhexan-2-yl)carbamate (17 g) for 30 minutes, followed by stirring at room temperature for 14 hours. The solvent was distilled away from the reaction solution under reduced pressure, the obtained residue was purified by silica gel chromatography (n-hexane:ethyl acetate=5.5:1), and a yellow solid of (2S)-2-((tert-butoxycarbonyl)amino)hexane-3-yl 4-nitrobenzoate (17 g) was thus obtained.

Aufarbeitung

  1. distillationThe solvent was distilled away from the reaction solution under reduced pressure
  2. customthe obtained residue was purified by silica gel chromatography (n-hexane:ethyl acetate=5.5:1)

Quellen und Nachweise

ORD-Eintrag
ord-44aa852be7c1423898b3a2ff746c57a8
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08895585B2

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