Trifluoroacetic acid → 4-[2-(4-Ethyl-4-oxido-1,4-azaphosphinan-1-yl)-2-oxoethyl]benzoic acid

HRID 1013513Notes

Reaction equation

HRID 1013513 reaction equation
[CH2:1]([P:3]1(=[O:25])[CH2:8][CH2:7][N:6]([C:9](=[O:24])[CH2:10][C:11]2[CH:23]=[CH:22][C:14]([C:15]([O:17]C(C)(C)C)=[O:16])=[CH:13][CH:12]=2)[CH2:5][CH2:4]1)[CH3:2].C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH2:1]([P:3]1(=[O:25])[CH2:8][CH2:7][N:6]([C:9](=[O:24])[CH2:10][C:11]2[CH:23]=[CH:22][C:14]([C:15]([OH:17])=[O:16])=[CH:13][CH:12]=2)[CH2:5][CH2:4]1)[CH3:2]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 57925996tert-Butyl 4-[2-(4-ethyl-4-oxido-1,4-azaphosphinan-1-yl)-2-oxoethyl]benzoate

Product 1

HCID 579259254-[2-(4-Ethyl-4-oxido-1,4-azaphosphinan-1-yl)-2-oxoethyl]benzoic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-Butyl 4-[2-(4-ethyl-4-oxido-1,4-azaphosphinan-1-yl)-2-oxoethyl]benzoate (270 mg, 0.739 mmol) was dissolved in CH2Cl2 (8 mL) and TFA (2 mL) and stirred at room temperature for 2 h. The solution was concentrated to dryness, redissolved in MeOH, and concentrated again to give the product as a colorless gum that was carried on without purification. MS: cal'd 310 (MH+), exp 310 (MH+).

Workup

  1. concentrationThe solution was concentrated to dryness
  2. dissolutionredissolved in MeOH
  3. concentrationconcentrated again

Sources & evidence

ORD record
ord-aae72704cdbb4ffdb00dfcd78b23778a
Source dataset
uspto-grants-2011_07
Patent number
US07981874B2

Reaction notes

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