Sodium Hydroxide → (3S)-3-amino-2-hydroxy-N-[(1R)-1-phenylethyl]heptanamide

HRID 1180735

Reaktionsgleichung

Reaktionsgleichung von HRID 1180735
C([O:9][CH:10]([C:27]([NH:29][C@@H:30]([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[CH3:31])=[O:28])[C@@H:11]([NH:16]C(OCC1C=CC=CC=1)=O)[CH2:12][CH2:13][CH2:14][CH3:15])(=O)C1C=CC=CC=1.[OH-].[Na+]>O1CCOCC1.O>[NH2:16][C@@H:11]([CH2:12][CH2:13][CH2:14][CH3:15])[CH:10]([OH:9])[C:27]([NH:29][C@@H:30]([C:32]1[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1)[CH3:31])=[O:28]

Komponenten

5

Edukt 2

HCID 14798Sodium HydroxideHCID 11202880(2S)-2-{[(benzyloxy)carbonyl]amino}-1-({[(1R)-1-phenylethyl]amino}carbonyl)hexyl benzoate

Produkt 1

HCID 11265560(3S)-3-amino-2-hydroxy-N-[(1R)-1-phenylethyl]heptanamideAusbeute 95,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittel2×HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

A mixture of 8.75 g (17.4 mmol) of (2S)-2-{[(benzyloxy)carbonyl]amino}-1-({[(1R)-1-phenylethyl]amino}carbonyl)hexyl benzoate and 6.97 g (174 mmol) of sodium hydroxide in 175 mL of dioxane and 75 mL of water was heated to reflux for 3 h and then let cool to room temperature. The reaction was diluted with 100 mL of water and extracted with ethyl acetate. The combined ethyl acetate layers were dried over potassium carbonate and concentrated to afford 4.38 g (95%) of (3S)-3-amino-2-hydroxy-N-[(1R)-1-phenylethyl]heptanamide as a white solid. 1H NMR (300 MHz, DMSO-d6) δ 8.08 (d, J=8 Hz, 1H), 7.39-7.20 (m, 5H), 4.99 (m, 1H), 4.51 (bs, 1H), 3.71 (d, J=3 Hz, 1H), 2.81 (m, 1H), 1.50-1.05 (m, 9H), 0.87 (t, 3H). ES-LCMS m/z 265 (M+H).

Aufarbeitung

  1. temperaturewas heated
  2. temperatureto reflux for 3 h
  3. extractionextracted with ethyl acetate
  4. dry with materialThe combined ethyl acetate layers were dried over potassium carbonate
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-7850d10ac8cc483ba3c2a56ee02f5556
Quelldatensatz
uspto-grants-2007_10
Patentnummer
US07282512B2

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