Trifluoroacetic acid → 2-[[[2-(Benzylcarboxy)propyl]hydroxyphosphinyl]-methyl]pentanedioic acid

HRID 842593Notes

Reaction equation

HRID 842593 reaction equation
[CH2:1]([O:8][C:9]([CH:11]([CH3:38])[CH2:12][P:13]([CH2:20][CH:21]([CH2:29][CH2:30][C:31]([O:33]C(C)(C)C)=[O:32])[C:22]([O:24]C(C)(C)C)=[O:23])([O:15]C(C)(C)C)=[O:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.FC(F)(F)C(O)=O>ClCCl>[CH2:1]([O:8][C:9]([CH:11]([CH3:38])[CH2:12][P:13]([CH2:20][CH:21]([CH2:29][CH2:30][C:31]([OH:33])=[O:32])[C:22]([OH:24])=[O:23])([OH:15])=[O:14])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 18418074Di-tert-butyl 2-[[[2-(benzylcarboxy)propyl]tert-butoxyphosphinyl]methyl]pentanedioate

Product 1

HCID 187257142-[[[2-(Benzylcarboxy)propyl]hydroxyphosphinyl]-methyl]pentanedioic acidYield 72%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of di-tert-butyl 2-[[[2-(benzylcarboxy)propyl]tert-butoxyphosphinyl]methyl]pentane-1,5-dioate (1.6 g, 2.89 mmol) in dichloromethane (10 ml) under nitrogen was added trifluoroacetic acid (10 ml). The reaction mixture was stirred for two hours and then concentrated under reduced pressure. Additional dichloromethane was added to the reaction residue and removed under reduced pressure. The product was dissolved in ethyl acetate and washed with water, then the organic layer was dried over magnesium sulfate and the solvent was removed under reduced pressure leaving a clear oil (800 mg, 72%). 1H NMR (D2O): δ1.2 (m, 3H), 1.6-1.8 (m, 4H), 2.1 (m, 2H), 2.2 (m, 2H), 2.6 (m, 1H), 2.8 (m, 1H), 5.0 (m, 2H), 7.3 (m, 5H). Analysis calculated for C17H23PO8 1.0H2O: C, 50.50; H, 6.23. Found: C, 50.52; H, 5.92.

Workup

  1. concentrationconcentrated under reduced pressure
  2. additionAdditional dichloromethane was added to the reaction residue
  3. customremoved under reduced pressure
  4. dissolutionThe product was dissolved in ethyl acetate
  5. washwashed with water
  6. dry with materialthe organic layer was dried over magnesium sulfate
  7. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-ae17e0c3a02648d6b23097213c56db67
Source dataset
uspto-grants-2002_04
Patent number
US06376478B1

Reaction notes

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