Trifluoroacetic acid methylene chloride → HCID 59140384, compound

HRID 425435Notes

Reaction equation

HRID 425435 reaction equation
[CH:1]1([CH2:7][C:8]2[NH:12][C:11]([CH2:13][CH:14]([C:16]3[CH:21]=[CH:20][C:19]([C:22]4[C:23]([C:28]([O:30]C(C)(C)C)=[O:29])=[CH:24][CH:25]=[CH:26][CH:27]=4)=[CH:18][CH:17]=3)[CH3:15])=[N:10][CH:9]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(O)(C(F)(F)F)=O.C(Cl)Cl>>[CH:1]1([CH2:7][C:8]2[NH:12][C:11]([CH2:13][CH:14]([C:16]3[CH:17]=[CH:18][C:19]([C:22]4[C:23]([C:28]([OH:30])=[O:29])=[CH:24][CH:25]=[CH:26][CH:27]=4)=[CH:20][CH:21]=3)[CH3:15])=[N:10][CH:9]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

3

Reactant 2

HCID 21863450Trifluoroacetic acid methylene chlorideHCID 66705869HCID 66705869, compound

Product 1

HCID 59140384HCID 59140384, compound

Procedure

To a 25 mL one neck round bottom flask was added tert-butyl 4′-{2-[5-(cyclohexylmethyl)-1H-imidazol-2-yl]-1-methylethyl}biphenyl-2-carboxylate (35.7 mg), which was treated with a mixture of TFA/CH2Cl2 (1.5 mL/1.5 mL) at rt for 2 hours. Then the solvent was removed by rotary evaporation and the resulting residue was coevaporated with toluene/H2O three times. The resulting crude product was purified by PrepTLC (2000 uM, 10% MeOH/CH2Cl2) to afford 4′-[2-[5-(cyclohexylmethyl)-1H-imidazol-2-yl]-1-methylethyl]-[1,1′-biphenyl]-2-carboxylic acid. 1HNMR (CD3OD, 500 MHz, ppm): 7.52 (1H, br), 7.38 (2H, br), 7.32 (2H, br), 7.28 (1H, br), 7.10 (2H, br), 6.87 (1H, s), 3.20 (1H, br), 3.08 (1H, br), 2.99 (1H, br), 2.41 (2 h, br), 1.58-1.73 (4H, m), 1.48 (1H, m), 1.32 (3H, br), 1.14-1.22 (4H, m), 0.88 (2H, m); m/z (ES) (M+H)+=403).

Workup

  1. customThen the solvent was removed by rotary evaporation
  2. customThe resulting crude product was purified by PrepTLC (2000 uM, 10% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-49441ce1351b46fe8932deb8183c3ab9
Source dataset
uspto-grants-2012_01
Patent number
US08106070B2

Reaction notes

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