Trifluoroacetic acid → HCID 25013303, compound

HRID 1013469Notes

Reaction equation

HRID 1013469 reaction equation
[CH2:1]([O:3][P:4]([CH2:7][C:8]1[CH:13]=[CH:12][C:11]([C:14](=[O:35])[NH:15][C:16]2[CH:21]=[C:20]([C:22]3[S:23][CH:24]=[CH:25][CH:26]=3)[CH:19]=[CH:18][C:17]=2[NH:27]C(OC(C)(C)C)=O)=[CH:10][CH:9]=1)([CH3:6])=[O:5])[CH3:2].C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH2:1]([O:3][P:4]([CH2:7][C:8]1[CH:9]=[CH:10][C:11]([C:14](=[O:35])[NH:15][C:16]2[CH:21]=[C:20]([C:22]3[S:23][CH:24]=[CH:25][CH:26]=3)[CH:19]=[CH:18][C:17]=2[NH2:27])=[CH:12][CH:13]=1)([CH3:6])=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 57925911HCID 57925911, compound

Product 1

HCID 25013303HCID 25013303, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of [4-(2-tert-butoxycarbonylamino-5-thiophen-2-yl-phenylcarbamoyl)-benzyl]-methyl-phosphinic acid ethyl ester (500 mg, 0.972 mmol) in DCM (10 mL) was added TFA (5 mL, 64.9 mmol). After 2 h, the solvent was removed, and to the residue was added EtOAc and sat. NaHCO3. The aqueous fraction was extracted further with EtOAc, dried (MgSO4), filtered and the solvent was evaporated under reduced pressure. The material was used without further purification. 1H NMR (DMSO-d6) δ 9.69 (br s, 1H), 7.92 (d, J=7.9 Hz, 2H), 7.44 (m, 1H), 7.39 (dd, J=7.9, 2.0 Hz, 1H), 7.33 (dd, J=5.0, 1.8 Hz, 1H), 7.27 (dd, J=8.2, 2.0 Hz, 1H), 7.21 (dd, J=3.5, 1.0 Hz, 1H), 7.02 (dd, J=5.0, 3.5 Hz, 1H), 6.78 (d, J=8.2 Hz, 1H), 5.13 (s, 2H), 3.97-3.88 (m, 2H), 3.40-3.25 (m, 2H), 1.32 (d, J=13.8 Hz, 3H), 1.27 (t, J=7.0 Hz, 3H). MS: cal'd 415 (MH+), exp 415 (MH+).

Workup

  1. customthe solvent was removed
  2. additionto the residue was added EtOAc and sat. NaHCO3
  3. extractionThe aqueous fraction was extracted further with EtOAc
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customthe solvent was evaporated under reduced pressure
  7. customThe material was used without further purification

Sources & evidence

ORD record
ord-95369a8784c747ac82a1835ca3f1c029
Source dataset
uspto-grants-2011_07
Patent number
US07981874B2

Reaction notes

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