3,5-Xylyl isocyanate → HCID 70558281, Verbindung

HRID 408615Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 408615
Cl.[CH3:2][O:3][C:4](=[O:24])[CH2:5][CH2:6][CH2:7][N:8]([CH2:16][C:17]1[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=1)[C:9]([C:11]1([CH3:15])[CH2:14][CH2:13][NH:12]1)=[O:10].[CH3:25][C:26]1[CH:27]=[C:28]([N:33]=[C:34]=[O:35])[CH:29]=[C:30]([CH3:32])[CH:31]=1>C1COCC1>[CH3:2][O:3][C:4](=[O:24])[CH2:5][CH2:6][CH2:7][N:8]([CH2:16][C:17]1[CH:18]=[CH:19][C:20]([Cl:23])=[CH:21][CH:22]=1)[C:9]([C:11]1([CH3:15])[CH2:14][CH2:13][N:12]1[C:34](=[O:35])[NH:33][C:28]1[CH:29]=[C:30]([CH3:32])[CH:31]=[C:26]([CH3:25])[CH:27]=1)=[O:10]

Komponenten

4

Edukt 2

HCID 5214883,5-Xylyl isocyanateHCID 70557278HCID 70557278, Verbindung

Produkt 1

HCID 70558281HCID 70558281, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
20 °C

Versuchsvorschrift

To a solution of 4-[(4-chloro-benzyl)-(2-methyl-azetidine-2-carbonyl)-amino]-butyric acid methyl ester hydrochloride, Intermediate 23 (1 eq.) and TEA (5 eq.) in THF under nitrogen was added 3,5-dimethyl-phenyl-isocyanate (1.5 eq.). The reaction was stirred for 15 h at 20° C. The crude was partitioned between a saturated aqueous solution of NaHCO3 and EtOAc. The organic layer was washed with water and brine, dried over MgSO4, filtered and concentrated under reduced pressure. The crude was purified by chromatography on silica gel (elution with heptane/EtOAc: 75/25 to 40/60) to afford 4-{(4-chloro-benzyl)-[1-(3,5-dimethyl-phenylcarbamoyl)-2-methyl-azetidine-2-carbonyl]-amino}-butyric acid methyl ester.

Aufarbeitung

  1. customThe crude was partitioned between a saturated aqueous solution of NaHCO3 and EtOAc
  2. washThe organic layer was washed with water and brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe crude was purified by chromatography on silica gel (elution with heptane/EtOAc: 75/25 to 40/60)

Quellen und Nachweise

ORD-Eintrag
ord-d2bb5d29b6034cd5905b00c286bd6f73
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08759334B2

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