1-Butanol → (S)-2-(4-((2-Amino-4-(2-hydroxybutylamino)-6-methylpyrimidin-5-yl)methyl)phenyl)acetic acid

HRID 1617235

Reaktionsgleichung

Reaktionsgleichung von HRID 1617235
[OH-:1].[K+].C([CH2:5][C:6]1[CH:32]=[CH:31][C:9]([CH2:10][C:11]2[C:12]([N:23]3[CH2:27][C@H:26]([CH2:28][CH3:29])[O:25]C3=O)=[N:13][C:14](/[N:18]=C/N(C)C)=[N:15][C:16]=2[CH3:17])=[CH:8][CH:7]=1)#N.[CH2:33]([OH:37])CCC>>[NH2:18][C:14]1[N:13]=[C:12]([NH:23][CH2:27][C@@H:26]([OH:25])[CH2:28][CH3:29])[C:11]([CH2:10][C:9]2[CH:8]=[CH:7][C:6]([CH2:5][C:33]([OH:37])=[O:1])=[CH:32][CH:31]=2)=[C:16]([CH3:17])[N:15]=1

Komponenten

4

Edukt 3

HCID 2631-ButanolHCID 14797Potassium HydroxideHCID 87445299N'-[5-[[4-(cyanomethyl)phenyl]methyl]-4-[(5S)-5-ethyl-2-oxo-1,3-oxazolidin-3-yl]-6-methylpyrimidin-2-yl]-N,N-dimethylmethanimidamide

Produkt 1

HCID 68414496(S)-2-(4-((2-Amino-4-(2-hydroxybutylamino)-6-methylpyrimidin-5-yl)methyl)phenyl)acetic acid

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

Aq. 5M KOH (1 ml) was added to a stirred solution of the product from step (vi) (136 mg) in butan-1-ol (2 mL). The solution was heated at 100° C. for 15 h and the solvent evaporated under reduced pressure. The residue was diluted with MeOH (2 mL) and the pH adjusted to ˜7 using acetic acid. The solution was purified by RPHPLC to give the subtitle compound as a white solid, 55 mg.

Aufarbeitung

  1. customthe solvent evaporated under reduced pressure
  2. additionThe residue was diluted with MeOH (2 mL)
  3. customThe solution was purified by RPHPLC

Quellen und Nachweise

ORD-Eintrag
ord-106272be15604e57b604f2f3281df270
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08765939B2

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