4-(2-t-Butoxycarbonylaminoethyl)phenoxymethyl phosphonic acid, diethyl ester → 4-(2-Aminoethyl)phenoxymethylphosphonic acid, diethyl ester

HRID 1528Notes

Reaction equation

HRID 1528 reaction equation
C(OC([NH:8][CH2:9][CH2:10][C:11]1[CH:26]=[CH:25][C:14]([O:15][CH2:16][P:17](=[O:24])([O:21][CH2:22][CH3:23])[O:18][CH2:19][CH3:20])=[CH:13][CH:12]=1)=O)(C)(C)C>C(Cl)Cl.FC(F)(F)C(O)=O>[NH2:8][CH2:9][CH2:10][C:11]1[CH:12]=[CH:13][C:14]([O:15][CH2:16][P:17](=[O:24])([O:18][CH2:19][CH3:20])[O:21][CH2:22][CH3:23])=[CH:25][CH:26]=1

Participants

4

Reactant 1

HCID 867521914-(2-t-Butoxycarbonylaminoethyl)phenoxymethyl phosphonic acid, diethyl ester

Product 1

HCID 541187064-(2-Aminoethyl)phenoxymethylphosphonic acid, diethyl ester

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

4-(2-t-Butoxycarbonylaminoethyl)phenoxymethylphosphonic acid, diethyl ester (2.856 g, 9.95 mMol) in methylene chloride (300 ml) and trifluoracetic acid (16 ml) was stirred at room temperature for 5 h. The solution was concentrated under reduced pressure and product dried under in vacuo. The trifluoacetic acid salt was neutralized with aqueous sodium carbonate and extracted with dichloromethane containing a small proportion of methanol (5×100 ml). The combined organic layers were dried over sodium sulfate and evaporated to dryness to give the title compound as a pale yellow gum.

Workup

  1. concentrationThe solution was concentrated under reduced pressure and product
  2. customdried under in vacuo
  3. extractionextracted with dichloromethane containing a small proportion of methanol (5×100 ml)
  4. dry with materialThe combined organic layers were dried over sodium sulfate
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-37aef411031a48079180fe910acb60fa
Source dataset
uspto-grants-1998_03
Patent number
US05726165

Reaction notes

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