Trifluoroacetic acid → HCID 178502923, compound

HRID 1013470Notes

Reaction equation

HRID 1013470 reaction equation
C(OC([NH:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[S:16][CH:17]=[CH:18][CH:19]=2)=[CH:11][C:10]=1[NH:20][C:21]([C:23]1[CH:34]=[CH:33][C:26]([CH2:27][CH2:28][PH:29](=[O:32])[O:30][CH3:31])=[CH:25][CH:24]=1)=[O:22])=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[S:16][CH:17]=[CH:18][CH:19]=2)=[CH:11][C:10]=1[NH:20][C:21]([C:23]1[CH:24]=[CH:25][C:26]([CH2:27][CH2:28][PH:29](=[O:32])[O:30][CH3:31])=[CH:33][CH:34]=1)=[O:22]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 178502924HCID 178502924, compound

Product 1

HCID 178502923HCID 178502923, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methyl [4-({[2-[(tert-butoxycarbonyl)amino]-5-(2-thienyl)phenyl]amino}carbonyl)benzyl]methyl-phosphinate (6.69 g, 13.37 mmol) was dissolved in CH2Cl2 (48 ml), and TFA (12 ml) was added. The solution was stirred at room temperature for 3 h and evaporated. The residue was dissolved in CH2Cl2, washed with saturated NaHCO3 and brine, dried (MgSO4), and evaporated. The crude was then slurried in CH2Cl2 and triturated with a small amount of hexanes to precipitate the title compound as a colorless solid. This material was subjected to chiral SFC to provide enantiopure samples of the two enantiomeric forms. Spectral data for racemate: 1H NMR (DMSO-d6) δ 9.68 (s, 1H), 7.92 (d, J=7.9 Hz, 2H), 7.44 (d, J=1.6 Hz, 1H), 7.38 (dd, J=8.1, 2.0 Hz, 2H), 7.32 (dd, J=5.2, 0.9 Hz, 1H), 7.27 (dd, J=8.3, 2.2 Hz, 1H), 7.21 (d, J=3.6 Hz, 1H), 7.01 (dd, J=5.0, 3.6 Hz, 1H), 6.78 (d, J=8.7 Hz, 1H), 5.13 (s, 2H), 3.55 (d, J=11.0 Hz, 3H), 3.29 (d, J=18.0 Hz, 2H), 1.32 (d, J=13.7 Hz, 3H). MS: cal'd 401 (MH+), exp 401 (MH+).

Workup

  1. customevaporated
  2. dissolutionThe residue was dissolved in CH2Cl2
  3. washwashed with saturated NaHCO3 and brine
  4. dry with materialdried (MgSO4)
  5. customevaporated
  6. customtriturated with a small amount of hexanes
  7. customto precipitate the title compound as a colorless solid
  8. customto provide enantiopure samples of the two enantiomeric forms

Sources & evidence

ORD record
ord-0156c7935225401ead6187fc67eb166a
Source dataset
uspto-grants-2011_07
Patent number
US07981874B2

Reaction notes

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