Phosphate → Trichloroethyl alpha-amino-diethylphosphonoacetate

HRID 1658002Notes

Reaction equation

HRID 1658002 reaction equation
C1(C)C=CC(S(O)(=O)=O)=CC=1.[NH2:12][CH:13]([P:22]([O:27][CH2:28][CH3:29])([O:24][CH2:25][CH3:26])=[O:23])[C:14]([O:16][CH2:17][C:18]([Cl:21])([Cl:20])[Cl:19])=[O:15].P([O-])([O-])([O-])=O>C(Cl)Cl>[NH2:12][CH:13]([P:22]([O:24][CH2:25][CH3:26])([O:27][CH2:28][CH3:29])=[O:23])[C:14]([O:16][CH2:17][C:18]([Cl:20])([Cl:21])[Cl:19])=[O:15]

Participants

4

Reactant 2

HCID 1061PhosphateHCID 21529973Trichloroethyl alpha-amino-diethylphosphonoacetate p-toluenesulfonate

Product 1

HCID 21529974Trichloroethyl alpha-amino-diethylphosphonoacetateYield 97.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trichloroethyl α-amino-diethylphosphonoacetate p-toluenesulfonate (1.03 g., 2 mmole) is partitioned between methylene chloride (20 ml.) and aqueous phosphate (4 ml. 1M dipotassium phosphate + 6 ml. water). The aqueous phase (pH 6.8) is separated and extracted with an additional portion of methylene chloride (10 ml.). The combined organic solution is washed with saturated brine (10 ml.), dried over magnesium sulfate, and evaporated in vacuo to give trichloroethyl α-amino-diethylphosphonoacetate (0.67 g.) as a pale yellow oil.

Workup

  1. customThe aqueous phase (pH 6.8) is separated
  2. extractionextracted with an additional portion of methylene chloride (10 ml.)
  3. washThe combined organic solution is washed with saturated brine (10 ml.)
  4. dry with materialdried over magnesium sulfate
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-4abc70a87d9947f190d5ba0223faee9e
Source dataset
uspto-grants-1976_06
Patent number
US03962224

Reaction notes

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