Lithium hydroxide, monohydrate → (R)-2-((S)-1-Hydroxy-2-morpholin-4-yl-2-oxo-ethyl)-5-phenyl-pentanoic acid

HRID 1830159Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1830159
C[O:2][C:3](=[O:24])[C@@H:4]([C@H:14]([OH:23])[C:15]([N:17]1[CH2:22][CH2:21][O:20][CH2:19][CH2:18]1)=[O:16])[CH2:5][CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.O[Li].O>C1COCC1.O>[OH:23][C@@H:14]([C@@H:4]([CH2:5][CH2:6][CH2:7][C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[C:3]([OH:24])=[O:2])[C:15]([N:17]1[CH2:22][CH2:21][O:20][CH2:19][CH2:18]1)=[O:16]

Komponenten

5

Edukt 2

HCID 168937Lithium hydroxide, monohydrateHCID 69434738(R)-2-((S)-1-Hydroxy-2-morpholin-4-yl-2-oxo-ethyl)-5-phenyl-pentanoic acid methyl ester

Produkt 1

HCID 58619483(R)-2-((S)-1-Hydroxy-2-morpholin-4-yl-2-oxo-ethyl)-5-phenyl-pentanoic acidAusbeute 81,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittel2×HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

A solution of (R)-2-((S)-1-hydroxy-2-morpholin-4-yl-2-oxo-ethyl)-5-phenyl-pentanoic acid methyl ester (230 mg, 0.69 mmol) and LiOH.H2O (57.5 mg, 1.37 mmol) in a mixture of THF and water (2:1, 6 ml) was stirred at room temperature for 2.5 hrs. The reaction was diluted with water and THF removed under reduced pressure. The pH of the aqueous solution was adjusted to pH5 with 1N HCl and extracted with ethyl acetate. The combined organic extracts were dried over MgSO4 and evaporated under reduced pressure to give the title compound as white solid (180 mg); 1H NMR (CDCl3) δ 1.92–1.60 (m, 4H), 2.75–2.60 (m, 3H), 3.78–3.45 (m, 9H), 4.5 (d, J=8 Hz, 1H), 7.35–7.18 (m, 5H); MS: 322(MH+).

Aufarbeitung

  1. customremoved under reduced pressure
  2. extractionextracted with ethyl acetate
  3. dry with materialThe combined organic extracts were dried over MgSO4
  4. customevaporated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-a29d8dea58a341b189e912cdf0d97097
Quelldatensatz
uspto-grants-2006_06
Patentnummer
US07064123B1

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