Acetic Acid → HCID 68455471, Verbindung

HRID 502387Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 502387
[CH2:1]([O:3][C:4](=[O:24])[C:5]([CH3:23])([O:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([C:14](=[O:22])[NH:15][CH:16]2[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]2)[CH:9]=1)[CH3:6])[CH3:2].[CH2:25]([O:27][C:28]1[CH:29]=[C:30]([CH:33]=[C:34]([O:37][CH2:38][CH3:39])[C:35]=1[F:36])[CH:31]=O)[CH3:26].C(N(C(C)C)C(C)C)C.C(O)(=O)C.C([BH3-])#N.[Na+].C(=O)([O-])[O-].[Na+].[Na+]>CO>[CH2:1]([O:3][C:4](=[O:24])[C:5]([O:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([C:14](=[O:22])[NH:15][CH:16]2[CH2:17][CH2:18][N:19]([CH2:31][C:30]3[CH:33]=[C:34]([O:37][CH2:38][CH3:39])[C:35]([F:36])=[C:28]([O:27][CH2:25][CH3:26])[CH:29]=3)[CH2:20][CH2:21]2)[CH:9]=1)([CH3:23])[CH3:6])[CH3:2]

Komponenten

8

Edukt 6

HCID 176Acetic AcidHCID 10340Sodium CarbonateHCID 81531DiisopropylethylamineHCID 5003444Sodium cyanoborohydrideHCID 591282733,5-Diethoxy-4-fluoro-benzaldehydeHCID 684563992-Methyl-2-[3-(piperidin-4-ylcarbamoyl)-phenoxy]-propionic acid ethyl ester

Produkt 1

HCID 68455471HCID 68455471, VerbindungAusbeute 94,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

0.33 g (1.0 mmol) of 2-methyl-2-[3-(piperidin-4-ylcarbamoyl)-phenoxy]-propionic acid ethyl ester and 0.23 g (1.10 eq.) of 3,5-diethoxy-4-fluoro-benzaldehyde (example 50 g), were dissolved under argon in 6 mL of MeOH; 0.39 mL (0.29 g=2.25 eq.) of N-ethyl-diisopropylamine and 0.11 mL (0.12 g=2.0 eq.) of glacial acetic acid were added and the mixture then heated for 2 h at 50° C. After cooling down to rt, 0.16 g (2.5 eq.) of sodium cyanoborohydride was added and the reaction mixture heated again for 1.5 h at 50° C. It was then poured into crashed ice, the pH was adjusted to ˜10 with sodium carbonate solution and the mixture was extracted twice with MeCl2; the organic phases were washed with water, dried over MgSO4, filtered and evaporated i.V. The crude product was purified by chromatography (silicagel, eluent:gradient of MeCl2/MeOH) to yield 0.50 g of the title compound as colorless oil. MS: 531.2 (MH+).

Aufarbeitung

  1. temperatureAfter cooling down to rt
  2. temperaturethe reaction mixture heated again for 1.5 h at 50° C
  3. additionIt was then poured
  4. extractionthe mixture was extracted twice with MeCl2
  5. washthe organic phases were washed with water
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. customevaporated i.V
  9. customThe crude product was purified by chromatography (silicagel, eluent:gradient of MeCl2/MeOH)

Quellen und Nachweise

ORD-Eintrag
ord-eadb32a43a4d4cd3ab64e35be937ef18
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07772253B2

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