Sodium Hydroxide → (R)-1-{2-[3-(5-methyl-2-phenyl-oxazol-4-ylmethoxy)-phenyl]-acetyl}-pyrrolidine-2-carboxylic acid

HRID 1994069Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1994069
C([O:3][C:4]([C@H:6]1[CH2:10][CH2:9][CH2:8][N:7]1[C:11](=[O:33])[CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([O:19][CH2:20][C:21]2[N:22]=[C:23]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[O:24][C:25]=2[CH3:26])[CH:14]=1)=[O:5])C.[OH-].[Na+]>CO>[CH3:26][C:25]1[O:24][C:23]([C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)=[N:22][C:21]=1[CH2:20][O:19][C:15]1[CH:14]=[C:13]([CH2:12][C:11]([N:7]2[CH2:8][CH2:9][CH2:10][C@@H:6]2[C:4]([OH:5])=[O:3])=[O:33])[CH:18]=[CH:17][CH:16]=1

Komponenten

4

Edukt 2

HCID 14798Sodium HydroxideHCID 68675365HCID 68675365, Verbindung

Produkt 1

HCID 11247155(R)-1-{2-[3-(5-methyl-2-phenyl-oxazol-4-ylmethoxy)-phenyl]-acetyl}-pyrrolidine-2-carboxylic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

To a solution of the title B compound, (R)-1-{2-[3-(5-methyl-2-phenyl-oxazol-4-ylmethoxy)-phenyl]-acetyl}-pyrrolidine-2-carboxylic acid ethyl ester (1.3 g, 2.9 mmol) in 25 mL of methanol at RT is added 1 N aqueous sodium hydroxide (8.7 mL). The mixture is stirred for 20 h and washed with ethyl acetate. The aqueous layer is acidified with 1 N aqueous hydrochloric acid (HCl), extracted with ethyl acetate, washed with brine, dried over anhydrous sodium sulfate and concentrated to give an oil. The crude product is purified by flash chromatography (silica gel) eluting with ethyl acetate→ethyl acetate:acetic acid (2:1) to give (R)-1-{2-[3-(5-methyl-2-phenyl-oxazol-4-ylmethoxy)-phenyl]-acetyl}-pyrrolidine-2-carboxylic acid as a foam: MS m/z 419.1 [M−1]−.

Aufarbeitung

  1. washwashed with ethyl acetate
  2. extractionextracted with ethyl acetate
  3. washwashed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated
  6. customto give an oil
  7. customThe crude product is purified by flash chromatography (silica gel)
  8. washeluting with ethyl acetate→ethyl acetate:acetic acid (2:1)

Quellen und Nachweise

ORD-Eintrag
ord-6b9e3591fad44e77b69c090521cc4941
Quelldatensatz
uspto-grants-2010_01
Patentnummer
US07652061B2

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