Sodium Hydroxide → HCID 18387433, Verbindung

HRID 2296760Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2296760
[NH2:1][CH2:2][CH2:3][C:4]1[S:5][C:6]2[CH:32]=[CH:31][CH:30]=[CH:29][C:7]=2[N:8]([CH2:12][C:13]2[CH:18]=[CH:17][C:16]([NH:19][C:20](=[O:28])[C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[CH3:27])=[CH:15][CH:14]=2)[C:9](=[O:11])[CH:10]=1.[CH3:33][O:34][C:35]1[CH:42]=[C:41]([O:43][CH3:44])[CH:40]=[CH:39][C:36]=1[CH:37]=O.C([BH3-])#N.[Na+].[OH-].[Na+]>CO.C(O)(=O)C>[CH3:33][O:34][C:35]1[CH:42]=[C:41]([O:43][CH3:44])[CH:40]=[CH:39][C:36]=1[CH2:37][NH:1][CH2:2][CH2:3][C:4]1[S:5][C:6]2[CH:32]=[CH:31][CH:30]=[CH:29][C:7]=2[N:8]([CH2:12][C:13]2[CH:14]=[CH:15][C:16]([NH:19][C:20](=[O:28])[C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[CH3:27])=[CH:17][CH:18]=2)[C:9](=[O:11])[CH:10]=1

Komponenten

7

Edukt 4

HCID 14798Sodium HydroxideHCID 691752,4-DimethoxybenzaldehydeHCID 5003444Sodium cyanoborohydrideHCID 18387460HCID 18387460, Verbindung

Produkt 1

HCID 18387433HCID 18387433, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidLösungsmittelHCID 887MethanolLösungsmittel

Versuchsvorschrift

A mixture of Compound 7 as prepared in Example 31 (0.105 g, 0.24 mM), 2,4-dimethoxybenzaldehyde (0.040 g, 0.240 mM) and acetic acid (0.05 ml) in methanol was stirred at room temperature for three hours and 2.5 equivalence of sodium cyanoborohydride was added. The mixture was stirred at room temperature for an additional 4 hours and a 6N NaOH (0.5 ml; adjusted to pH8) was added. The methanol was removed under reduced pressure and the residue diluted with water (50 ml) and extracted with ethyl acetate (2×5 ml). The ethyl acetate extracts were dried (MgSO4), evaporated in vacuo and purified by flash column chromatography (EM silica gel 60; 5% MeOH in CH2Cl2) to give a white solid product. m/z (MH+) 596.

Aufarbeitung

  1. stirringThe mixture was stirred at room temperature for an additional 4 hours
  2. customThe methanol was removed under reduced pressure
  3. additionthe residue diluted with water (50 ml)
  4. extractionextracted with ethyl acetate (2×5 ml)
  5. dry with materialThe ethyl acetate extracts were dried (MgSO4)
  6. customevaporated in vacuo
  7. custompurified by flash column chromatography (EM silica gel 60; 5% MeOH in CH2Cl2)
  8. customto give a white solid product

Quellen und Nachweise

ORD-Eintrag
ord-6e572664b85d464ea3e3c0c265f84a7b
Quelldatensatz
uspto-grants-2002_12
Patentnummer
US06489321B1

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