Ammonium Hydroxide → Ethyl 3-amino-2-fluoro-1-methyl-3-oxopropyl(methyl)phosphinate

HRID 1358211Notes

Reaction equation

HRID 1358211 reaction equation
[CH2:1]([O:3][P:4]([CH:7]([CH3:15])[CH:8]([F:14])[C:9](OCC)=[O:10])([CH3:6])=[O:5])[CH3:2].[OH-].[NH4+:17]>C(O)C>[NH2:17][C:9](=[O:10])[CH:8]([F:14])[CH:7]([P:4]([CH3:6])(=[O:5])[O:3][CH2:1][CH3:2])[CH3:15]

Participants

4

Reactant 2

HCID 14923Ammonium Hydroxide2×HCID 18184131HCID 18184131, compound

Product 1

HCID 18184128Ethyl 3-amino-2-fluoro-1-methyl-3-oxopropyl(methyl)phosphinateYield 91.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of ethyl 3-[ethoxy(methyl)phosphoryl]-2-fluorobutanoate (3.0 g, 12.4 mmol) in ethanol (15 mL) was added concentrated ammonium hydroxide (14.8 M, 1.3 mL, 19 mmol). The solution was stirred for 24 h at room temperature and then at 50° C. for 2 hours. Another portion of concentrated ammonium hydroxide (14.8 M, 0.5 mL, 7 mmol) was added and the mixture was stirred at room temperature for three days and then evaporated to give 2.4 g (91%) of a diastereomeric mixture of ethyl 3-amino-2-fluoro-1-methyl-3-oxopropyl(methyl)phosphinate as a clear oil. 1H NMR (400 MHz, CDCl3) δ5.9-6.7 (m, 2H), 4.9-5.6 (m, 1H), 4.0-4.2 (m, 2H), 2.5-2.8 (m, 1H), 1.2-1.6 (m, 9H).

Workup

  1. waitat 50° C. for 2 hours
  2. stirringthe mixture was stirred at room temperature for three days
  3. customevaporated

Sources & evidence

ORD record
ord-ddf5989b15af45cb9d94e3ee154f6fd4
Source dataset
uspto-grants-2003_07
Patent number
US06596711B1

Reaction notes

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