Trifluoroacetic acid → HCID 9848666, compound

HRID 1373349Notes

Reaction equation

HRID 1373349 reaction equation
[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([C:17]3[CH:22]=[CH:21][C:20]([O:23][C:24]([F:27])([F:26])[F:25])=[CH:19][CH:18]=3)=[CH:14][CH:15]=2)[C:10]([C:28](=[O:40])[C:29]([NH:31][CH2:32][C:33]([O:35]C(C)(C)C)=[O:34])=[O:30])=[CH:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.FC(F)(F)C(O)=O>C(Cl)Cl>[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([C:17]3[CH:18]=[CH:19][C:20]([O:23][C:24]([F:25])([F:26])[F:27])=[CH:21][CH:22]=3)=[CH:14][CH:15]=2)[C:10]([C:28](=[O:40])[C:29]([NH:31][CH2:32][C:33]([OH:35])=[O:34])=[O:30])=[CH:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 22065230HCID 22065230, compound

Product 1

HCID 9848666HCID 9848666, compoundYield 77.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To an ice-cooled solution of tert-butyl 2-[(2-{1-benzyl-5-[4-(trifluoromethoxy)phenyl]-1H-indol-3-yl}-2-oxoacetyl)amino]acetate (1.33 g, 2.41 mmol) in methylene chloride (25 mL) was added 12 mL (160 mmol) of trifluoroacetic acid. The reaction mixture was stirred for two hours at room temperature then concentrated. The residue was crystallized twice from isopropanol. It was dried for 15 hours at 95° C. to give the title compound as yellow solid (0.928 g, 77%), mp 211–2° C. (dec.). Mass spectrum (−ESI, [M−H]−) m/z 495; 1HNMR (500 MHz, DMSO-d6): δ12.5–13.0 (br, 1H), 9.05 (s, 1H), 8.95 (t, 1H, J=6.1 Hz), 8.5 (d, 1H, J=1.5 Hz), 7.75–7.8 (m, 2H), 7.7 (d, 1H, J=8.6 Hz), 7.6 (dd, 1H, J=8.6 Hz and 1.8 Hz), 7.45 (d, 2H, J=8.1 Hz), 7.25–7.35 (m, 5H), 5.65 (s, 2H), and 3.9 ppm (d, 2H, J=6.1 Hz).

Workup

  1. concentrationthen concentrated
  2. customThe residue was crystallized twice from isopropanol
  3. customIt was dried for 15 hours at 95° C.

Sources & evidence

ORD record
ord-2fb1b5869b33455385ba9ac219593af4
Source dataset
uspto-grants-2007_01
Patent number
US07160918B2

Reaction notes

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