Triphenylphosphine → HCID 86587129, Verbindung

HRID 2084932Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2084932
[CH2:1]([O:5][C:6]1[CH:11]=[CH:10][C:9]([S:12]([NH:15][CH:16]([CH2:21]O)[C:17]([O:19][CH3:20])=[O:18])(=[O:14])=[O:13])=[CH:8][CH:7]=1)[C:2]#[C:3][CH3:4].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O>C1COCC1>[CH2:1]([O:5][C:6]1[CH:11]=[CH:10][C:9]([S:12]([N:15]2[CH2:21][CH:16]2[C:17]([O:19][CH3:20])=[O:18])(=[O:14])=[O:13])=[CH:8][CH:7]=1)[C:2]#[C:3][CH3:4]

Komponenten

5

Edukt 3

HCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 12016494N-[[4-(2-Butyn-1-yloxy)phenyl]sulfonyl]serine methyl ester

Produkt 1

HCID 86587129HCID 86587129, VerbindungAusbeute 58 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a THF solution (10 mL) of methyl 2-({[4-(2-butynyloxy)phenyl]sulfonyl}amino)-3-hydroxypropanoate (0.33 g, 1 mmol) and triphenylphosphine (0.32 g, 1.2 mmol), diethylazodicarboxylate (0.19 mL, 1.2 mmol) was added dropwise. The mixture was stirred at room temperature overnight. After removing the solvent, the residue was extracted with ether. The organic layer was washed with 1N NaHCO3, water and brine, dried over sodium sulfate, filtered and concentrated. The residue was purified by column chromatography on silica gel eluting with hexane:ethyl acetate (1:1) to provide 0.18 g of 1-({[4-(2-butynyloxy)phenyl]sulfonyl}-2-aziridinecarboxylic acid, methyl ester. Yield 58.0%. Electrospray Mass Spec 310.2(M+H)+.

Aufarbeitung

  1. customAfter removing the solvent
  2. extractionthe residue was extracted with ether
  3. washThe organic layer was washed with 1N NaHCO3, water and brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by column chromatography on silica gel eluting with hexane:ethyl acetate (1:1)

Quellen und Nachweise

ORD-Eintrag
ord-2b731932bb4b44298f172d1d059fd194
Quelldatensatz
uspto-grants-2004_04
Patentnummer
US06716833B2

Notizen zur Reaktion

Wird geladen…