Benzoyl chloride → HCID 14850751, compound

HRID 345316Notes

Reaction equation

HRID 345316 reaction equation
[P:1]([CH2:5][C@H:6]1[CH2:11][CH2:10][NH:9][C@@H:8]([C:12]([OH:14])=[O:13])[CH2:7]1)([OH:4])([OH:3])=[O:2].C(=O)([O-])[O-].[Na+].[Na+].[C:21](Cl)(=[O:28])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>O.[OH-].[Na+]>[C:21]([N:9]1[CH2:10][CH2:11][C@H:6]([CH2:5][P:1]([OH:3])([OH:4])=[O:2])[CH2:7][C@@H:8]1[C:12]([OH:14])=[O:13])(=[O:28])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

6

Reactant 3

HCID 7412Benzoyl chlorideHCID 10340Sodium CarbonateHCID 6604838113229-61-1

Product 1

HCID 14850751HCID 14850751, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 14798Sodium HydroxideSolvent

Procedure

To a solution of 200 mg of cis-4-phosphonomethyl-2-piperidinecarboxylic acid, 96 mg of sodium carbonate in 5 ml of water and 2.31 ml of 1N aqueous sodium hydroxide is added 119 mg of benzoyl chloride. The reaction mixture is stirred at room temperature for 16 hours and the solvent is removed in vacuo. The residue is dissolved in ethanol, the solution is filtered and evaporated to dryness. Crystallization from ethanol/ethyl acetate affords cis-1-benzoyl-4-phosphonomethyl-2-piperidinecarboxylic acid, m.p. 135°-145° dec.

Workup

  1. customthe solvent is removed in vacuo
  2. dissolutionThe residue is dissolved in ethanol
  3. filtrationthe solution is filtered
  4. customevaporated to dryness
  5. customCrystallization from ethanol/ethyl acetate

Sources & evidence

ORD record
ord-fb4e30f79fae4750bf5580933fd842e6
Source dataset
uspto-grants-1991_10
Patent number
US05057506

Reaction notes

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