Trifluoroacetic acid → 3-(4-[2-(2-Biphenyl-4-yl-5-methyl-oxazol-4-yl)-ethoxy]-2-{[(2,5-dichloro-thiophene-3-carbonyl)-amino]-methyl}-phenyl)-propionic acid

HRID 1181057Notes

Reaction equation

HRID 1181057 reaction equation
C([O:5][C:6](=[O:47])[CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:16][CH2:17][C:18]2[N:19]=[C:20]([C:24]3[CH:29]=[CH:28][C:27]([C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=4)=[CH:26][CH:25]=3)[O:21][C:22]=2[CH3:23])=[CH:11][C:10]=1[CH2:36][NH:37][C:38]([C:40]1[CH:44]=[C:43]([Cl:45])[S:42][C:41]=1[Cl:46])=[O:39])(C)(C)C.C1(OC)C=CC=CC=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[C:27]1([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[CH:28]=[CH:29][C:24]([C:20]2[O:21][C:22]([CH3:23])=[C:18]([CH2:17][CH2:16][O:15][C:12]3[CH:13]=[CH:14][C:9]([CH2:8][CH2:7][C:6]([OH:47])=[O:5])=[C:10]([CH2:36][NH:37][C:38]([C:40]4[CH:44]=[C:43]([Cl:45])[S:42][C:41]=4[Cl:46])=[O:39])[CH:11]=3)[N:19]=2)=[CH:25][CH:26]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 7519AnisoleHCID 589792743-(4-[2-(2-Biphenyl-4-yl-5-methyl-oxazol-4-yl)-ethoxy]-2-{[(2,5-dichloro-thiophene-3-carbonyl)-amino]-methyl}-phenyl)-propionic acid tert-butyl ester

Product 1

HCID 102828493-(4-[2-(2-Biphenyl-4-yl-5-methyl-oxazol-4-yl)-ethoxy]-2-{[(2,5-dichloro-thiophene-3-carbonyl)-amino]-methyl}-phenyl)-propionic acidYield 89.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of the 3-(4-[2-(2-biphenyl-4-yl-5-methyl-oxazol-4-yl)-ethoxy]-2-{[(2,5-dichloro-thiophene-3-carbonyl)-amino]-methyl}-phenyl)-propionic acid tert-butyl ester (367 mg, 0.531 mmol) in CH2Cl2 (20 mL) was treated with anisole (2.0 mL) then TFA (6.0 mL). The mixture was stirred at room temperature for 2 h and concentrated. The residue was co-evaporated with CCl4 three times, dried under vacuum, triturated with ether, and filtered to obtain the title compound as a white solid (301 mg, 73%). 1H NMR (400 MHz, DMSO-d6): δ 2.25 (s, 3H), 2.38 (t, 2H, J=8.3 Hz), 2.71 (t, 2H, J=7.3 Hz), 2.82 (t, 2H, J=6.3 Hz), 4.07 (t, 2H, J=6.6 Hz), 4.28 (d, 2H, J=4.9 Hz), 6.68 (d, 1H, J=9.3 Hz), 6.77 (s, 1H), 7.00 (d, 1H, J=8.3 Hz), 7.24 (s, 1H), 7.29 (t, 1H, J=5.9 Hz), 7.39 (t, 2H, J=7.8 Hz), 7.63 (t, 2H, J=7.8 Hz), 7.71 (d, 2H, J=8.3 Hz), 7.88 (d, 2H, J=8.3 Hz), 8.69 (t, 2H, J=5.9 Hz). MS (ES) m/e 635.1 [M+1].

Workup

  1. concentrationconcentrated
  2. customdried under vacuum
  3. customtriturated with ether
  4. filtrationfiltered

Sources & evidence

ORD record
ord-92d6b2b32988492ca55c28877c2269df
Source dataset
uspto-grants-2007_10
Patent number
US07282501B2

Reaction notes

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