Methanol → (S)-2-(4-((2-Amino-4-(1-hydroxyheptan-3-ylamino)-6-methylpyrimidin-5-yl)methyl)-3-fluorophenyl)acetic acid

HRID 2387837

Reaktionsgleichung

Reaktionsgleichung von HRID 2387837
[OH-:1].[K+].[NH2:3][C:4]1[N:9]=[C:8]([NH:10][C@@H:11]([CH2:15][CH2:16][CH2:17][CH3:18])[CH2:12][CH2:13][OH:14])[C:7]([CH2:19][C:20]2[CH:25]=[CH:24][C:23]([CH2:26][C:27]#N)=[CH:22][C:21]=2[F:29])=[C:6]([CH3:30])[N:5]=1.C[OH:32]>>[NH2:3][C:4]1[N:9]=[C:8]([NH:10][C@@H:11]([CH2:15][CH2:16][CH2:17][CH3:18])[CH2:12][CH2:13][OH:14])[C:7]([CH2:19][C:20]2[CH:25]=[CH:24][C:23]([CH2:26][C:27]([OH:32])=[O:1])=[CH:22][C:21]=2[F:29])=[C:6]([CH3:30])[N:5]=1

Komponenten

4

Edukt 3

HCID 887MethanolHCID 14797Potassium HydroxideHCID 68954091(S)-2-(4-((2-Amino-4-(1-hydroxyheptan-3-ylamino)-6-methylpyrimidin-5-yl)methyl)-3-fluorophenyl)acetonitrile

Produkt 1

HCID 68956559(S)-2-(4-((2-Amino-4-(1-hydroxyheptan-3-ylamino)-6-methylpyrimidin-5-yl)methyl)-3-fluorophenyl)acetic acid

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

A 5M aqueous solution of potassium hydroxide (0.58 mL) was added to a stirred solution of the product from step (iv) (0.11 g) in MeOH (1.5 mL). The mixture was heated at 70° C. for 15 h. The solvent was evaporated under reduced pressure and the aqueous residue was adjusted to pH ˜7 with concentrated HCl. The aqueous was extracted with EtOAc and the combined organic phase was dried, filtered and evaporated to the subtitle compound, 0.102 g.

Aufarbeitung

  1. customThe solvent was evaporated under reduced pressure
  2. extractionThe aqueous was extracted with EtOAc
  3. customthe combined organic phase was dried
  4. filtrationfiltered
  5. customevaporated to the subtitle compound, 0.102 g

Quellen und Nachweise

ORD-Eintrag
ord-11d56a098c7847de9bd273ca0ca243f5
Quelldatensatz
uspto-grants-2012_09
Patentnummer
US08268990B2

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