Acetic Acid → Acetic Acid [5-benzyloxy-4-methoxy-2-(5-methyl-[1,2,4]-oxadiazol-3-yl)phenyl]tert-butylcarbamoylmethyl Ester

HRID 2075956Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2075956
[CH2:1]([O:8][C:9]1[C:10]([O:23][CH3:24])=[CH:11][C:12]([C:17]2[N:21]=[C:20]([CH3:22])[O:19][N:18]=2)=[C:13]([CH:16]=1)[CH:14]=[O:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:25]([N+:29]#[C-:30])([CH3:28])([CH3:27])[CH3:26].[C:31](O)(=[O:33])[CH3:32].C(#N)C.[OH2:38]>C(OCC)(=O)C>[CH2:1]([O:8][C:9]1[C:10]([O:23][CH3:24])=[CH:11][C:12]([C:17]2[N:21]=[C:20]([CH3:22])[O:19][N:18]=2)=[C:13]([CH:14]([O:15][C:31](=[O:33])[CH3:32])[C:30](=[O:38])[NH:29][C:25]([CH3:28])([CH3:27])[CH3:26])[CH:16]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

7

Edukt 5

HCID 176Acetic AcidHCID 962WaterHCID 6342AcetonitrileHCID 23577Tert-Butyl isocyanideHCID 595656495-Benzyloxy-4-methoxy-2-(5-methyl-[1,2,4]oxadiazol-3-yl)benzaldehyde

Produkt 1

HCID 86647228Acetic Acid [5-benzyloxy-4-methoxy-2-(5-methyl-[1,2,4]-oxadiazol-3-yl)phenyl]tert-butylcarbamoylmethyl Ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

A mixture of 5-benzyloxy-4-methoxy-2-(5-methyl-[1,2,4]oxadiazol-3-yl)benzaldehyde (Reference example 15-1) (453 mg), tert-butylisocyanide (465 mg), acetic acid (0.32 mL) and acetonitrile (8 mL) was stirred at 70° C. for 13 hours. After cooling to room temperature, ethyl acetate and water were added to the mixture. The separated organic layer was washed with water, an aqueous solution of sodium bicarbonate, and brine successively, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: 15%-50% ethyl acetate/hexane, gradient elution) to give the title compound (604 mg).

Aufarbeitung

  1. temperatureAfter cooling to room temperature
  2. washThe separated organic layer was washed with water
  3. dry with materialan aqueous solution of sodium bicarbonate, and brine successively, dried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (eluent: 15%-50% ethyl acetate/hexane, gradient elution)

Quellen und Nachweise

ORD-Eintrag
ord-725ea753136447e5be442f51724feb1e
Quelldatensatz
uspto-grants-2011_04
Patentnummer
US07923462B2

Notizen zur Reaktion

Wird geladen…