Water → HCID 19084820, compound

HRID 962400Notes

Reaction equation

HRID 962400 reaction equation
[C:1]([CH2:3][CH2:4][C:5]([P:12]([O:17]CC)([O:14]CC)=[O:13])([OH:11])[C:6]([O:8]CC)=[O:7])#[N:2].C[Si](Br)(C)C.O>C(Cl)(Cl)Cl>[C:1]([CH2:3][CH2:4][C:5]([OH:11])([P:12]([OH:14])([OH:17])=[O:13])[C:6]([OH:8])=[O:7])#[N:2]

Participants

5

Reactant 3

HCID 962WaterHCID 76113BromotrimethylsilaneHCID 19084730HCID 19084730, compound

Product 1

HCID 19084820HCID 19084820, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A solution of 2.77 g (0.01 mole) of ethyl 4-cyano-2-diethoxyphosphinyl-2-hydroxybutanoate in 30 ml of CHCl3 is treated with 10.7 g (0.07 mole) of trimethylsilyl bromide. The solution is stirred at 50° for about one day. It's cooled to room temperature, and water is added. The mixture is stirred for about 30 minutes. The layers are separated, and the water layer is washed several times with CHCl3. The water layer is evaporated to dryness under vacuum, and the residue is triturated with acetone to convert it to a solid (filter to collect it), which is 4-cyano-2-hydroxy-2-phosphonobutanoic acid.

Workup

  1. stirringThe mixture is stirred for about 30 minutes
  2. customThe layers are separated
  3. washthe water layer is washed several times with CHCl3
  4. customThe water layer is evaporated to dryness under vacuum
  5. customthe residue is triturated with acetone
  6. filtrationto a solid (filter to collect it), which

Sources & evidence

ORD record
ord-9340bfdfa9de485da44fe985da9976c1
Source dataset
uspto-grants-1998_06
Patent number
US05760021

Reaction notes

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