Hydrochloric Acid → HCID 20376517, compound

HRID 2052725Notes

Reaction equation

HRID 2052725 reaction equation
[P:1]([CH:5]1[CH2:9][CH2:8][CH2:7][NH:6]1)([OH:4])([OH:3])=[O:2].[OH-].[Na+].[C:12]([S:15][CH:16]([CH3:20])[C:17](Cl)=[O:18])(=[O:14])[CH3:13].Cl>O>[C:12]([S:15][CH:16]([CH3:20])[C:17]([N:6]1[CH2:7][CH2:8][CH2:9][CH:5]1[P:1](=[O:4])([OH:3])[OH:2])=[O:18])(=[O:14])[CH3:13]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium Hydroxide2×HCID 12765068HCID 12765068, compoundHCID 13479534S-(1-Chloro-1-oxopropan-2-yl) ethanethioate

Product 1

HCID 20376517HCID 20376517, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2-Phosphonopyrrolidine is dissolved in water and the pH of the solution adjusted to 7 by the addition of sodium hydroxide. The solution is cooled in an ice bath, and 2-(acetylthio)propanoyl chloride is added dropwise. During the addition, the pH of the solution is maintained at 7 by the addition of 2 N sodium hydroxide. After the addition is complete, the reaction mixture is acidified to pH 2 with concentrated HCl and extracted with ethyl acetate. Drying (over MgSO4) and evaporation of the extracts affords a residue of the product, [1-(2-acetylthio-1-oxopropyl)-2-pyrrolidinyl]phosphonic acid.

Workup

  1. temperatureThe solution is cooled in an ice bath
  2. additionDuring the addition
  3. additionAfter the addition
  4. extractionextracted with ethyl acetate
  5. customDrying
  6. custom(over MgSO4) and evaporation of the extracts

Sources & evidence

ORD record
ord-63f7468179cf4d999d91a338fcff8390
Source dataset
uspto-grants-1980_01
Patent number
US04186268

Reaction notes

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