Sodium Hydroxide → N-{[(1R,3S,4S)-3-methoxy-4-(nitrooxy)cyclopentyl]carbonyl}-L-valine

HRID 41162

Reaktionsgleichung

Reaktionsgleichung von HRID 41162
[CH3:1][O:2][C@@H:3]1[C@@H:7]([O:8][N+:9]([O-:11])=[O:10])[CH2:6][C@H:5]([C:12]([NH:14][C@H:15]([C:19]([O:21]C)=[O:20])[CH:16]([CH3:18])[CH3:17])=[O:13])[CH2:4]1.[OH-].[Na+]>CCO>[CH3:1][O:2][C@@H:3]1[C@@H:7]([O:8][N+:9]([O-:11])=[O:10])[CH2:6][C@H:5]([C:12]([NH:14][C@H:15]([C:19]([OH:21])=[O:20])[CH:16]([CH3:18])[CH3:17])=[O:13])[CH2:4]1

Komponenten

4

Edukt 2

HCID 14798Sodium HydroxideHCID 86657845HCID 86657845, Verbindung

Produkt 1

HCID 46220211N-{[(1R,3S,4S)-3-methoxy-4-(nitrooxy)cyclopentyl]carbonyl}-L-valineAusbeute 81,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

To a solution of methyl N-{[(1R,3S,4S)-3-methoxy-4-(nitrooxy)cyclopentyl]carbonyl}-L-valinate (1.04 g, 3.27 mmol) in EtOH (10 mL) was added NaOH (5.0 N, 1.0 mL). After stirring at rt overnight, the mixture was partitioned between Et2O/H2O. The aq layer was extracted and acidified using 5.0 N HCl until pH-3 and then extracted with Et2O (50 mL). The organic layer was washed with brine (2×50 mL), dried over Na2SO4, and concentrated to give the title compound as a white solid (810 mg, yield 81%): 1H NMR (500 MHz, CDCl3) δ 6.70 (d, J=8.4, 1H), 5.40 (d, J=6.0, 1H), 4.53 (dd, J=4.6, 8.5, 1H), 3.93 (m, 1H), 3.48 (s, 3H), 3.03-2.96 (m, 1H), 2.53-2.46 (m, 1H), 2.38-2.20 (m, 3H), 2.08-2.02 (m, 1H), 1.01 (d, J=6.9, 3H), 0.97 (d, J=6.9, 3H).

Aufarbeitung

  1. customthe mixture was partitioned between Et2O/H2O
  2. extractionThe aq layer was extracted
  3. extractionextracted with Et2O (50 mL)
  4. washThe organic layer was washed with brine (2×50 mL)
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-05f34cbbad724863bc6281104eaf4030
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08530521B2

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