Acetic Acid → 4-[7-(5-{3-Chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1,2,4,5-tetrahydro-3H-3-benzazepin-3-yl]butanoic acid

HRID 1514278Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1514278
[Cl:1][C:2]1[CH:3]=[C:4]([C:12]2[O:16][N:15]=[C:14]([C:17]3[CH:35]=[CH:34][C:20]4[CH2:21][CH2:22][N:23]([CH2:26][CH2:27][CH2:28][C:29]([O:31]CC)=[O:30])[CH2:24][CH2:25][C:19]=4[CH:18]=3)[N:13]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH:9]([CH3:11])[CH3:10].[OH-].[Na+].C(O)(=O)C>C(O)C>[Cl:1][C:2]1[CH:3]=[C:4]([C:12]2[O:16][N:15]=[C:14]([C:17]3[CH:35]=[CH:34][C:20]4[CH2:21][CH2:22][N:23]([CH2:26][CH2:27][CH2:28][C:29]([OH:31])=[O:30])[CH2:24][CH2:25][C:19]=4[CH:18]=3)[N:13]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH:9]([CH3:10])[CH3:11]

Komponenten

5

Edukt 3

HCID 176Acetic AcidHCID 14798Sodium HydroxideHCID 59403483Ethyl 4-[7-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1,2,4,5-tetrahydro-3H-3-benzazepin-3-yl]butanoate

Produkt 1

HCID 441289864-[7-(5-{3-Chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1,2,4,5-tetrahydro-3H-3-benzazepin-3-yl]butanoic acidAusbeute 30,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A solution of ethyl 4-[7-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1,2,4,5-tetrahydro-3H-3-benzazepin-3-yl]butanoate (Preparation 50) (100 mg, 0.201 mmol) in ethanol (6 ml) was stirred at room temp and sodium hydroxide (1.5 ml, 3.00 mmol) added. The reaction mixture was stirred at room temperature for 90 mins and was then acidified with acetic acid to pH 5, and the mixture concentrated in vacuo. The resultant residue was dissolved in EtOAc (˜30 ml) and water (˜30 ml) and the layers partitioned, the aqueous was re-extracted with EtOAc (˜20 ml) and the combined organics were passed through a phase separation cartridge and the solvent reduced in vacuo. The residue was purified by trituration with methanol, the solid filtered and dried on the sinter to yield the title compound (30 mg, 0.061 mmol, 30% yield). δH (d6DMSO, 400 MHz): 8.19 (1H, s), 8.11 (1H, d), 7.79-7.90 (2H, m), 7.44 (1H, d), 7.34 (1H, d), 4.89 (1H, sept), 3.46-3.24 (2H, hidden under H2O peak), 3.01-2.93 (4H, m), 2.68-2.59 (4H, m), 2.28 (2H, t), 1.70 (2H, quintet) 1.37 (6H, d). MS (ES): C25H2835ClN3O4 requires 469; found 470 [M+H]+.

Aufarbeitung

  1. concentrationthe mixture concentrated in vacuo
  2. dissolutionThe resultant residue was dissolved in EtOAc (˜30 ml)
  3. customwater (˜30 ml) and the layers partitioned
  4. extractionthe aqueous was re-extracted with EtOAc (˜20 ml)
  5. customthe combined organics were passed through a phase separation cartridge
  6. customThe residue was purified by trituration with methanol
  7. filtrationthe solid filtered
  8. customdried on the sinter

Quellen und Nachweise

ORD-Eintrag
ord-e0e818ac94384b908e04cff4937e8845
Quelldatensatz
uspto-grants-2012_07
Patentnummer
US08222245B2

Notizen zur Reaktion

Wird geladen…