Acetic Acid → HCID 58494145, Verbindung

HRID 1942591Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1942591
[Cl:1][C:2]1[CH:3]=[C:4]([C:12]2[S:16][C:15]([C:17]3[C:18]([CH2:25][CH3:26])=[C:19]([CH:22]=[CH:23][CH:24]=3)[CH:20]=O)=[N:14][N:13]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH:9]([CH3:11])[CH3:10].[NH:27]1[CH2:30][CH:29]([CH2:31]C(OC)=O)[CH2:28]1.[C:36]([O-])(=[O:38])C.[Na+].CC(O)=[O:43]>CO>[Cl:1][C:2]1[CH:3]=[C:4]([C:12]2[S:16][C:15]([C:17]3[C:18]([CH2:25][CH3:26])=[C:19]([CH2:20][N:27]4[CH2:28][CH:29]([C:31]([O:38][CH3:36])=[O:43])[CH2:30]4)[CH:22]=[CH:23][CH:24]=3)=[N:14][N:13]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH:9]([CH3:10])[CH3:11]

Komponenten

6

Edukt 4

HCID 176Acetic AcidHCID 517045Sodium AcetateHCID 53408531Methyl (azetidin-3-yl)acetateHCID 584940093-(5-{3-Chloro-4-[(1-methylethyl)oxy]phenyl}-1,3,4-thiadiazol-2-yl)-2-ethylbenzaldehyde

Produkt 1

HCID 58494145HCID 58494145, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

To a solution of 3-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,3,4-thiadiazol-2-yl)-2-ethylbenzaldehyde (D11) (43 mg) and methyl 3-azetidinylacetate (92 mg) in methanol (10.00 mL) stirred at room temperature was added sodium acetate (45.6 mg) and AcOH (0.032 mL). The reaction mixture was stirred at room temperature for 10 min. Then the solvent was removed by evaporation. The residue was dissolved in dichloromethane (DCM) (10 mL), and sodium triacetoxyborohydride (70.7 mg) was added. Stirring continued for 2 h. Water was added to quench the reaction, and DCM was removed by evaporation. The mixture was extracted by EA 3 times. The combined organic solution was washed by brine, dried over anhydrous Na2SO4. The dried solution was filtered and concentrated to give crude methyl 1-{[3-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,3,4-thiadiazol-2-yl)-2-ethylphenyl]methyl}-3-azetidinecarboxylate (D13) (54 mg). MS (ES): C25H28ClN3O3S requires 485. found 486.0 (M+H+).

Aufarbeitung

  1. customThen the solvent was removed by evaporation
  2. dissolutionThe residue was dissolved in dichloromethane (DCM) (10 mL)
  3. additionsodium triacetoxyborohydride (70.7 mg) was added
  4. stirringStirring
  5. waitcontinued for 2 h
  6. additionWater was added
  7. customto quench
  8. customthe reaction, and DCM
  9. customwas removed by evaporation
  10. extractionThe mixture was extracted by EA 3 times
  11. washThe combined organic solution was washed by brine
  12. dry with materialdried over anhydrous Na2SO4
  13. filtrationThe dried solution was filtered
  14. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-038096f84c8c4f06a92861507b5817a1
Quelldatensatz
uspto-grants-2013_03
Patentnummer
US08389508B2

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