Ammonium Hydroxide → Ethyl (3-amino-2-fluoro-3-oxopropyl)(methyl)phosphinate

HRID 1358209Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1358209
[CH2:1]([O:3][P:4]([CH2:7][CH:8]([F:14])[C:9](OCC)=[O:10])([CH3:6])=[O:5])[CH3:2].[OH-].[NH4+:16]>C(O)C>[NH2:16][C:9](=[O:10])[CH:8]([F:14])[CH2:7][P:4]([CH3:6])(=[O:5])[O:3][CH2:1][CH3:2]

Komponenten

4

Edukt 2

HCID 14923Ammonium HydroxideHCID 18184129Ethyl 3-[ethoxy(methyl)phosphoryl]-2-fluoropropanoate

Produkt 1

HCID 86759072Ethyl (3-amino-2-fluoro-3-oxopropyl)(methyl)phosphinateAusbeute 86,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A solution of ethyl 3-[ethoxy(methyl)phosphoryl]-2-fluoropropanoate (12.6 g, 55.6 mmol), ethanol (15 mL), and concentrated ammonium hydroxide (14.8 N, 5.6 mL, 83 mmol) were stirred at room temperature for 16 h. The solvent was evaporated and the residue chromatographed on a wet-packed silica gel column (5.5×31 cm) eluting with 90:10 methylene chloride/methanol. The appropriate fractions were combined and evaporated to give 9.5 g (86%) of ethyl (3-amino-2-fluoro-3-oxopropyl)(methyl)phosphinate as a clear oil. Data: 1H NMR (300 MHz, CDCl3) δ6.62 (s, 1H), 6.33 (s, 1H), 5.10-5.42 (m, 1H), 4.02-4.18 (m, 2H), 2.19-2.70 (m, 2H), 1.60 (d, J=14 Hz, 3H), 1.34 (m, 3H)

Aufarbeitung

  1. customThe solvent was evaporated
  2. customthe residue chromatographed on a wet-packed silica gel column (5.5×31 cm)
  3. washeluting with 90:10 methylene chloride/methanol
  4. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-3a4f8c9182b244efbb4d45d38e64b8df
Quelldatensatz
uspto-grants-2003_07
Patentnummer
US06596711B1

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