Acetaldehyde → HCID 68763137, Verbindung

HRID 1628573Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1628573
[NH2:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[C:4]([NH2:9])[C:3]=1[NH:10][CH2:11][CH2:12][CH2:13][OH:14].Cl.[Cl:16][C:17]1[CH:22]=[C:21]([Cl:23])[CH:20]=[CH:19][C:18]=1[CH:24]([OH:29])[C:25](=N)OC.[CH:30](=O)[CH3:31].[C:33](O[BH-](OC(=O)C)OC(=O)C)(=O)[CH3:34].[Na+]>C(O)C.C(=O)([O-])O.[Na+].CO>[Cl:16][C:17]1[CH:22]=[C:21]([Cl:23])[CH:20]=[CH:19][C:18]=1[CH:24]([OH:29])[C:25]1[N:10]([CH2:11][CH2:12][CH2:13][OH:14])[C:3]2[C:2]([N:1]([CH2:30][CH3:31])[CH2:33][CH3:34])=[CH:7][C:6]([F:8])=[CH:5][C:4]=2[N:9]=1

Komponenten

8

Edukt 4

HCID 177AcetaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 68735949HCID 68735949, VerbindungHCID 68736952HCID 68736952, Verbindung

Produkt 1

HCID 68763137HCID 68763137, VerbindungAusbeute 17,4 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 702EthanolLösungsmittelHCID 887MethanolLösungsmittelHCID 516892Sodium BicarbonateLösungsmittel

Versuchsvorschrift

A solution of 3-[(2,6-diamino-4-fluorophenyl)amino]propan-1-ol (498 mg, 2.50 mmol) and methyl 2-(2,4-dichlorophenyl)-2-hydroxyethanimidoate hydrochloride (812 mg, 3.00 mmol) in ethanol (5 mL) was stirred for 12 h at room temperature. The reaction mixture was diluted with aqueous sodium hydrogen carbonate, extracted with ethyl acetate, washed with brine, dried over sodium sulfate, filtrated, and concentrated in vacuo. The residue was dissolved in acetic acid (1.2 mL) and methanol (25 mL), and acetaldehyde (935 μL, 15.0 mmol) was added at 0° C. After 30 min, sodium triacetoxyborohydride (3.18 g, 15.0 mmol) was added. After 6 h, the reaction mixture was quenched with water, concentrated in vacuo, diluted with ethyl acetate, washed with aqueous sodium hydroxide (1 M) and brine, dried over sodium sulfate, filtered and concentrated in vacuo. The residue was purified by column chromatography on silica gel eluting with a 10-50% ethyl acetate/n-hexane gradient mixture to give the title compound as a colorless solid (192 mg, 0.436 mmol, 17%).

Aufarbeitung

  1. extractionextracted with ethyl acetate
  2. washwashed with brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltrated
  5. concentrationconcentrated in vacuo
  6. dissolutionThe residue was dissolved in acetic acid (1.2 mL)
  7. waitAfter 6 h
  8. customthe reaction mixture was quenched with water
  9. concentrationconcentrated in vacuo
  10. additiondiluted with ethyl acetate
  11. washwashed with aqueous sodium hydroxide (1 M) and brine
  12. dry with materialdried over sodium sulfate
  13. filtrationfiltered
  14. concentrationconcentrated in vacuo
  15. customThe residue was purified by column chromatography on silica gel eluting with a 10-50% ethyl acetate/n-hexane gradient mixture

Quellen und Nachweise

ORD-Eintrag
ord-fc3c433d51994b44a038c776928d8f41
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08785460B2

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