Benzyl Bromide → HCID 19084731, compound

HRID 962395Notes

Reaction equation

HRID 962395 reaction equation
[CH3:1][N:2]([CH2:4][CH2:5][C:6]([OH:14])([P:10]([OH:13])([OH:12])=[O:11])[C:7]([OH:9])=[O:8])[CH3:3].[OH-].[Na+].[CH2:17]([Br:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>O.C(O)C>[Br-:24].[C:7]([C:6]([OH:14])([P:10]([OH:13])([OH:12])=[O:11])[CH2:5][CH2:4][N+:2]([CH3:3])([CH3:1])[CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)([OH:9])=[O:8]

Participants

6

Reactant 3

HCID 7498Benzyl BromideHCID 14798Sodium HydroxideHCID 190848044-(N,N-dimethylamino)-2-hydroxy-2-phosphonobutanoic acid

Product 1

HCID 19084731HCID 19084731, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A solution of 2.27 g (0.01 mole) of 4-(N,N-dimethylamino)-2-hydroxy-2-phosphonobutanoic acid (prepared as described in Method 1) in 10 ml water and 40 ml ethanol is adjusted to pH 7.0 by addition of IN aqueous NaOH. To this is added 5.13 g (0.03 mole) of benzyl bromide, and the reaction is heated at about 50° for one day. The reaction is evaporated to dryness under reduced pressure. The resulting residue is slurried in water and the mixture is extracted several times with CHCl3. The aqueous solution is evaporated a little to get rid of traces of chloroform, and is treated with cation ion exchange resin in H+ form. The resin is filtered off, the aqueous solution is concentrated to a few ml, and ethanol is added dropwise to precipitate the product. This is purified by recrystallization from water/ethanol to give N-(3-carboxy-3-hydroxy-3-phosphonopropyl)-N,N-dimethyl-N-(phenylmethyl)ammonium bromide.

Workup

  1. temperaturethe reaction is heated at about 50° for one day
  2. customThe reaction is evaporated to dryness under reduced pressure
  3. extractionthe mixture is extracted several times with CHCl3
  4. customThe aqueous solution is evaporated a little
  5. customto get rid of traces of chloroform
  6. additionis treated with cation ion exchange resin in H+ form
  7. filtrationThe resin is filtered off
  8. concentrationthe aqueous solution is concentrated to a few ml, and ethanol
  9. additionis added dropwise
  10. customto precipitate the product
  11. customThis is purified by recrystallization from water/ethanol

Sources & evidence

ORD record
ord-a10a60104d04429a946ef7e600cb95c6
Source dataset
uspto-grants-1998_06
Patent number
US05760021

Reaction notes

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