Triphenylphosphine → HCID 59497701, Verbindung

HRID 1747437Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1747437
[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].[CH3:17][C:18]1[CH:19]=[C:20]2[N:25]([C:26]=1[CH3:27])[CH:24]=[CH:23][CH:22]=[C:21]2[CH2:28]O.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.[Al]>[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]([CH2:28][C:21]2[C:20]3[N:25]([C:26]([CH3:27])=[C:18]([CH3:17])[CH:19]=3)[CH:24]=[CH:23][CH:22]=2)[C:7]1=[O:15]

Komponenten

7

Edukt 4

HCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 59497358HCID 59497358, VerbindungHCID 59497624HCID 59497624, Verbindung

Produkt 1

HCID 59497701HCID 59497701, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 5359268AluminumLösungsmittel

Versuchsvorschrift

To a stirred solution of the 3-(2-oxo-2,3-dihydro-benzimidazol-1-yl)-propionic acid methyl ester (100 mg, 0.45 mmol) and (2,3-Dimethyl-indolizin-8-yl)-methanol (88 mg, 0.50 mmol) in THF (8 ml) was added triphenylphosphine (143 mg, 0.54 mmol) followed by DIAD (0.11 ml, 0.54 mmol, dropwise) at ambient temperature. After five minutes the reaction became dark brown and was consequently wrapped in aluminum foil. After stirring over night the reaction was treated with silica gel and concentrated. The remaining solid was purified via column chromatography (silica gel, 5-40% EtOAc/hexanes). The product-containing fractions were combined and concentrated to give the product which was used without further purification.

Aufarbeitung

  1. customat ambient temperature
  2. additionwas treated with silica gel
  3. concentrationconcentrated
  4. customThe remaining solid was purified via column chromatography (silica gel, 5-40% EtOAc/hexanes)
  5. concentrationconcentrated
  6. customto give the product which
  7. customwas used without further purification

Quellen und Nachweise

ORD-Eintrag
ord-302f2cec82584d83870362dc59a19ea3
Quelldatensatz
uspto-grants-2015_10
Patentnummer
US09150556B2

Notizen zur Reaktion

Wird geladen…