Trifluoroacetic acid → HCID 59347649, compound

HRID 20884Notes

Reaction equation

HRID 20884 reaction equation
C(OC([NH:8][C@H:9]([C:13]1[NH:14][C:15]([C:18]2[CH:23]=[CH:22][C:21]([C:24]3[CH:29]=[CH:28][C:27]([C:30]4[NH:34][C:33]([C@@H:35]5[CH2:39][CH2:38][CH2:37][N:36]5C(OC(C)(C)C)=O)=[N:32][CH:31]=4)=[CH:26][CH:25]=3)=[CH:20][CH:19]=2)=[CH:16][N:17]=1)[CH:10]([CH3:12])[CH3:11])=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH3:11][CH:10]([CH3:12])[C@@H:9]([C:13]1[NH:14][C:15]([C:18]2[CH:23]=[CH:22][C:21]([C:24]3[CH:29]=[CH:28][C:27]([C:30]4[NH:34][C:33]([C@@H:35]5[CH2:39][CH2:38][CH2:37][NH:36]5)=[N:32][CH:31]=4)=[CH:26][CH:25]=3)=[CH:20][CH:19]=2)=[CH:16][N:17]=1)[NH2:8]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59347693HCID 59347693, compound

Product 1

HCID 59347649HCID 59347649, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (S)-tert-butyl 2-(5-(4′-(2-((S)-1-(tert-butoxycarbonylamino)-2-methylpropyl)-1H-imidazol-5-yl)biphenyl-4-yl)-1H-imidazol-2-yl)pyrrolidine-1-carboxylate (2.05 g, 3.27 mmol) in CH2Cl2 (20 mL) was added TFA (5 mL, 64.9 mmol) and the solution was allowed to stir for 2 h. The solvents were removed in vacuo, the residue was dissolved in CH2Cl2: MeOH (1:1) (ca. 10 mL) and absorbed onto an MCX cation exchange cartridge (Oasis). The resin was washed with MeOH and the desired material was released by elution with NH3 in MeOH (2M). The solvents were removed in vacuo to afford the title compound (0.622 g, 91%) as a yellow foam which was sufficiently pure for use in subsequent steps. 1HNMR (500 MHz, CD3OD) δ 7.85-7.88 (m, 4H), 7.75 (m, app d, J=8.2 Hz, 4H), 7.70 (app d, J=5.8 Hz, 2H), 4.96 (t, J=8.2 Hz, 1H), 4.30 (d, J=8.5 Hz, 1H), 3.54-3.57 (m, 1H), 3.47-3.52 (m, 1H), 2.55-2.62 (m, 1H), 2.38-2.46 (m, 1H), 2.28-2.36 (m, 1H), 2.15-2.24 (m, 1H), 1.17 (d, J=6.7 Hz, 3H), 0.94 (d, J=6.7 Hz, 3H). LCMS: Anal. Calcd. for C26H30N6: 426; found: 427 (M+H)+.

Workup

  1. customThe solvents were removed in vacuo
  2. dissolutionthe residue was dissolved in CH2Cl2: MeOH (1:1) (ca. 10 mL)
  3. customabsorbed onto an MCX cation exchange cartridge (Oasis)
  4. washThe resin was washed with MeOH
  5. washthe desired material was released by elution with NH3 in MeOH (2M)
  6. customThe solvents were removed in vacuo

Sources & evidence

ORD record
ord-86b6518b7d9043a3ac31adc56fa29dc8
Source dataset
uspto-grants-2010_06
Patent number
US07745636B2

Reaction notes

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