Triphenylphosphine → HCID 86722610, Verbindung

HRID 2271499Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2271499
[NH:1]1[CH:5]=[N:4][N:3]=[N:2]1.[Cl:6][C:7]1[CH:8]=[C:9]([CH:14](O)[CH:15]2[CH2:18][N:17]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:16]2)[CH:10]=[CH:11][C:12]=1[Cl:13].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>O1CCCC1>[Cl:6][C:7]1[CH:8]=[C:9]([CH:14]([N:2]2[N:3]=[N:4][CH:5]=[N:1]2)[CH:15]2[CH2:18][N:17]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:16]2)[CH:10]=[CH:11][C:12]=1[Cl:13]

Komponenten

6

Edukt 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 594467411-Azetidinecarboxylic acid, 3-[(3,4-dichlorophenyl)hydroxymethyl]-, 1,1-dimethylethyl esterHCID 178418441HCID 178418441, Verbindung

Produkt 1

HCID 86722610HCID 86722610, VerbindungAusbeute 88 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

Tetrazole (90.0 mg, 1.28 mmol) was added to tertiary butyl 3-((3,4-dichlorophenyl)(hydroxy)methyl)azetidine-1-carboxylate (200 mg, 0.638 mmol) and triphenylphosphine (335 mg, 1.28 mmol) dissolved in the distilled tetrahydrofuran solution (15.0 mL), and diisopropyl azocarboxylate (0.25 mL, 1.28 mmol) was slowly added thereto at 0° C., and the mixture was stirred at room temperature for one day. The solvent of the reaction mixture was removed by reduced pressure evaporation to obtain a yellow liquid, which was purified by flash chromatography (n-hexane:ethyl acetate (4:1, v/v)). The product was identified as a single compound by TLC (n-hexane:ethyl acetate (4:1, v/v)) (yield: 88%, white solid). This white solid was dissolved in 10 mL of methanol solution, and 1 N HCl (3.0 mL) was added thereto, and heated to reflux at 60° C. for one day. Thereafter, the solvent of the reaction mixture was removed by reduced pressure evaporation to obtain the title compound (KHG27280).

Aufarbeitung

  1. additionwas slowly added
  2. customThe solvent of the reaction mixture was removed by reduced pressure evaporation
  3. customto obtain a yellow liquid, which
  4. customwas purified by flash chromatography (n-hexane:ethyl acetate (4:1
  5. dissolutionThis white solid was dissolved in 10 mL of methanol solution
  6. addition1 N HCl (3.0 mL) was added
  7. temperatureheated
  8. temperatureto reflux at 60° C. for one day
  9. customThereafter, the solvent of the reaction mixture was removed by reduced pressure evaporation

Quellen und Nachweise

ORD-Eintrag
ord-8a41be24fdcf4e57a2c0c6a2848c75fe
Quelldatensatz
uspto-grants-2015_09
Patentnummer
US09120771B2

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