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

HRID 1358209Notes

Reaction equation

HRID 1358209 reaction equation
[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]

Participants

4

Reactant 2

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

Product 1

HCID 86759072Ethyl (3-amino-2-fluoro-3-oxopropyl)(methyl)phosphinateYield 86.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

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)

Workup

  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

Sources & evidence

ORD record
ord-3a4f8c9182b244efbb4d45d38e64b8df
Source dataset
uspto-grants-2003_07
Patent number
US06596711B1

Reaction notes

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