Triphenylphosphine → HCID 66643884, Verbindung

HRID 1695327Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1695327
[CH3:1][O:2][C:3]([C:5]1[NH:6][N:7]=[C:8]([OH:10])[CH:9]=1)=[O:4].[CH3:11][C:12]1[O:16][N:15]=[C:14]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:13]=1[CH2:23]O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>C1COCC1>[CH3:1][O:2][C:3]([C:5]1[NH:6][N:7]=[C:8]([O:10][CH2:23][C:13]2[C:14]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[N:15][O:16][C:12]=2[CH3:11])[CH:9]=1)=[O:4]

Komponenten

6

Edukt 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 2776149(5-Methyl-3-phenyl-1,2-oxazol-4-yl)methanolHCID 1784986025-Hydroxy-1H-pyrazole-3-carboxylic acid methyl ester

Produkt 1

HCID 66643884HCID 66643884, VerbindungAusbeute 27,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a stirred solution of 5-hydroxy-2H-pyrazole-3-carboxylic acid methyl ester (1.30 g, 9.15 mmol) and (5-methyl-3-phenyl-isoxazol-4-yl)-methanol (1.73 g, 9.15 mmol) in THF (80 mL) at 5° C. under argon was added triphenylphosphine (3.12 g, 11.9 mmol), then diethyl azodicarboxylate (2.07 g, 11.9 mmol) was added dropwise. The reaction mixture was warmed to room temperature and stirred overnight. The reaction mixture was then evaporated. Purification by chromatography (silica, heptane:ethyl acetate=1:1 then dichloromethane:methanol=9:1) gave a colorless oil (800 mg) which was triturated with diisopropylether and further purified using a 5×50 cm Chiralpak AD column at room temperature using an isopropanol:heptane (2:8) mobile phase with UV detection at 220 nM to afford the title compound (250 mg, 9%) as a white solid. MS: m/e=328.3 [M+H]+.

Aufarbeitung

  1. customThe reaction mixture was then evaporated
  2. customPurification by chromatography (silica, heptane

Quellen und Nachweise

ORD-Eintrag
ord-27ba284d6b304aacbbd8eb4a79295903
Quelldatensatz
uspto-grants-2012_04
Patentnummer
US08163728B2

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