Ammonium → HCID 86586172, compound

HRID 1760378Notes

Reaction equation

HRID 1760378 reaction equation
[CH2:1]([O:3][CH:4]([O:18][CH2:19][CH3:20])[P:5]([CH2:10][CH:11]([F:17])[C:12](OCC)=[O:13])([O:7][CH2:8][CH3:9])=[O:6])[CH3:2].[NH4+:21]>C(O)C>[NH2:21][C:12](=[O:13])[CH:11]([F:17])[CH2:10][P:5]([CH:4]([O:18][CH2:19][CH3:20])[O:3][CH2:1][CH3:2])(=[O:6])[O:7][CH2:8][CH3:9]

Participants

4

Reactant 2

HCID 223AmmoniumHCID 22178372HCID 22178372, compound

Product 1

HCID 86586172HCID 86586172, compoundYield 27%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of ethyl 3-[(diethoxymethyl)(ethoxy)phosphoryl]-2-fluoropropanoate (16.0 g, 51.1 mmol) in ethanol (22 mL) was added concentrated ammonium hydroxyde (14.8 N, 3.5 mL, 51.1 mmol). The solution was stirred for 16 h and evaporated. The residue was purified by chromatography on a wet-packed silica gel column (7×37 cm) eluting with 96.5:3.5 methylene chloride/methanol. The appropriate fractions were combined and evaporated to give 3.43 g (27%) of ethyl (3-amino-2-fluoro-3-oxopropyl)(diethoxymethyl)phosphinate as a clear oil. Data: 1H NMR (300 MHz, CDCl3) δ 6.43 (s, 1H), 5.70 (s, 1H), 5.21-5.49 (dm, 1H), 4.7 (dd, 1H), 4.18-4.31 (m, 2H), 3.65-3.91 (m, 4H), 2.21-2.81 (m, 2H), 1.30-1.40 (m, 3H), 1.20-1.28 (m, 6H).

Workup

  1. customevaporated
  2. customThe residue was purified by chromatography on a wet-packed silica gel column (7×37 cm)
  3. washeluting with 96.5:3.5 methylene chloride/methanol
  4. customevaporated

Sources & evidence

ORD record
ord-c15e298d7854494c8aaeb83d6b2869c3
Source dataset
uspto-grants-2005_01
Patent number
US06841698B2

Reaction notes

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