(2-Aminoethyl)phosphonic acid → (2-{[(Benzyloxy)carbonyl]amino}ethyl)phosphonic acid

HRID 853646Notes

Reaction equation

HRID 853646 reaction equation
[NH2:1][CH2:2][CH2:3][P:4](=[O:7])([OH:6])[OH:5].[OH-].[Na+].Cl[C:11]([O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:12]>>[C:11]([NH:1][CH2:2][CH2:3][P:4](=[O:6])([OH:5])[OH:7])([O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:12]

Participants

4

Reactant 3

HCID 339(2-Aminoethyl)phosphonic acidHCID 10387Benzyl chloroformateHCID 14798Sodium Hydroxide

Product 1

HCID 13368880(2-{[(Benzyloxy)carbonyl]amino}ethyl)phosphonic acidYield 91%

Procedure

To a solution of 2-aminoethylphosphonic acid (1.26 g, 10.1 mmol) in 2N NaOH (10.1 mL, 20.2 mmol) was added benzyl chloroformate (1.7 mL, 12.1 mmol). After the reaction mixture was stirred for 2 d at room temperature, the mixture was partitioned between Et2O and water. The aqueous phase was acidified with 6N HCl until pH=2. The resulting colorless solid was dissolved in MeOH (75 mL) and treated with Dowex 50WX8-200 (7 g). After the mixture was stirred for 30 minutes, it was filtered and evaporated under reduced pressure to give carbobenzoxyaminoethyl phosphonic acid (2.37 g, 91%) as a colorless solid.

Workup

  1. customthe mixture was partitioned between Et2O and water
  2. dissolutionThe resulting colorless solid was dissolved in MeOH (75 mL)
  3. additiontreated with Dowex 50WX8-200 (7 g)
  4. stirringAfter the mixture was stirred for 30 minutes
  5. filtrationit was filtered
  6. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-0e3111fb3c894f36b4eaefc6d6307953
Source dataset
uspto-grants-2007_08
Patent number
US07253180B2

Reaction notes

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