Sodium Hydroxide → HCID 19084786, compound

HRID 962396Notes

Reaction equation

HRID 962396 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+].[C:17]([S:20][CH2:21][CH2:22][Br:23])(=[O:19])[CH3:18]>O.C(O)C>[Br-:23].[C:17]([S:20][CH2:21][CH2:22][N+:2]([CH2:4][CH2:5][C:6]([C:7]([OH:9])=[O:8])([OH:14])[P:10]([OH:13])([OH:12])=[O:11])([CH3:1])[CH3:3])(=[O:19])[CH3:18]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 523036Ethanethioic acid, S-(2-bromoethyl) esterHCID 190848044-(N,N-dimethylamino)-2-hydroxy-2-phosphonobutanoic acid

Product 1

HCID 19084786HCID 19084786, 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 20 ml water and 40 ml ethanol is adjusted to pH 7.0 by addition of 1N aqueous NaOH. To this is added 9.16 g (0.05 mole) of S-acetyl-2-bromoethanethiol, and the reaction is heated at 40°-80° for several hours. The reaction is evaporated to dryness under reduced pressure. The resulting residue is triturated with acetone several times (acetone extracts are discarded). The remaining solid is dissolved in distilled water, and is treated with cation exchange resin in H+ form. The resin is filtered off, the aqueous solution is concentrated to a few ml, and acetone is added dropwise to precipitate the product. This is purified by recrystallization from water/acetone to give N-(2-(acetylthio)ethyl)-N-(3-carboxy-3-hydroxy-3-phosphonopropyl)-N,N-dimethylammonium bromide.

Workup

  1. temperaturethe reaction is heated at 40°-80° for several hours
  2. customThe reaction is evaporated to dryness under reduced pressure
  3. customThe resulting residue is triturated with acetone several times (acetone extracts are discarded)
  4. dissolutionThe remaining solid is dissolved in distilled water
  5. additionis treated with cation exchange resin in H+ form
  6. filtrationThe resin is filtered off
  7. concentrationthe aqueous solution is concentrated to a few ml, and acetone
  8. additionis added dropwise
  9. customto precipitate the product
  10. customThis is purified by recrystallization from water/acetone

Sources & evidence

ORD record
ord-70229989750548c9970e601333aca494
Source dataset
uspto-grants-1998_06
Patent number
US05760021

Reaction notes

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