Triphenylphosphine → HCID 59497299, Verbindung

HRID 1747351Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1747351
[CH3:1][O:2][C:3](=[O:16])[CH2:4][CH2:5][N:6]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[NH:8][C:7]1=[O:15].[C:17]([Si:21]([CH3:36])([CH3:35])[O:22][C:23]1[CH:24]=[C:25]2[C:30](=[CH:31][CH:32]=1)[C:29]([CH2:33]O)=[CH:28][CH:27]=[CH:26]2)([CH3:20])([CH3:19])[CH3:18].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1COCC1>[CH3:1][O:2][C:3](=[O:16])[CH2:4][CH2:5][N:6]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[N:8]([CH2:33][C:29]2[C:30]3[C:25](=[CH:24][C:23]([O:22][Si:21]([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:36])[CH3:35])=[CH:32][CH:31]=3)[CH:26]=[CH:27][CH:28]=2)[C:7]1=[O:15]

Komponenten

6

Edukt 4

HCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 59497358HCID 59497358, VerbindungHCID 59497482HCID 59497482, Verbindung

Produkt 1

HCID 59497299HCID 59497299, VerbindungAusbeute 60 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a stirred solution of 3-(2-oxo-2,3-dihydro-benzimidazol-1-yl)-propionic acid methyl ester (180 mg, 0.82 mmol) in THF (12 ml) was added [6-(tert-butyl-dimethyl-silanyloxy)-naphthalen-1-yl]-methanol (283 mg, 0.98 mmol) and triphenylphosphine (257 mg, 0.98 mmol). The DIAD (0.20 ml, 0.98 mmol) was then introduced in a dropwise manner and the resulting mixture was stirred at ambient temperature over night. Silica gel was added and the reaction mixture was concentrated to dryness. The resulting solid was purified via column chromatography (silica gel, 40% ethyl acetate/hexanes) to give 240 mg (60%) of the desired product as an oil which solidified on standing.

Aufarbeitung

  1. additionSilica gel was added
  2. concentrationthe reaction mixture was concentrated to dryness
  3. customThe resulting solid was purified via column chromatography (silica gel, 40% ethyl acetate/hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-3540f009fddf428abe1addc9cf843668
Quelldatensatz
uspto-grants-2015_10
Patentnummer
US09150556B2

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