Trifluoroacetic acid → HCID 22065225, compound

HRID 1828224Notes

Reaction equation

HRID 1828224 reaction equation
[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([O:23][C:24]([F:27])([F:26])[F:25])[CH:18]=3)=[CH:14][CH:15]=2)[C:10]([C:28](=[O:41])[C:29]([N:31]([CH3:40])[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:22]=[CH:21][CH:20]=[C:19]([O:23][C:24]([F:25])([F:26])[F:27])[CH:18]=3)=[CH:14][CH:15]=2)[C:10]([C:28](=[O:41])[C:29]([N:31]([CH3:40])[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 22065229HCID 22065229, compound

Product 1

HCID 22065225HCID 22065225, compoundYield 60.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To an ice-cooled solution of tert-butyl 2-[(2-{1-benzyl-5-[3-(trifluoromethoxy)phenyl]-1H-indol-3-yl}-2-oxoacetyl)(methyl)amino]acetate (5.17 g, 9.13 mmol) in methylene chloride (60 mL) was added trifluoroacetic acid (30 mL, 390 mmol). The reaction mixture was stirred for 1.5 hours at room temperature and concentrated. The residue was treated with diethyl ether and the mixture was concentrated to the precipitation point. The solid was purified by HPLC using 70% acetonitrile/0.1% formic acid in water as the mobile phase. The acetonitrile was evaporated, and the aqueous phase was extracted with ethyl acetate and washed with water and brine. The organic phase was evaporated to dryness and the residue was dried for 15 hours at 91° C. to give the title compound as a light pink solid (2.81 g, 60%), mp 178–179° C. Mass spectrum (−ESI, [M-H]−) m/z 509; 1HNMR (500 MHz, DMSO-d6): δ12.8–13.2 (br,1H), 8.45 (m, 1H), 8.35 (d, 1H, J=8.4 Hz), 7.7–7.8 (m, 3H), 7.55–7.65 (m, 2H), 7.4–7.45 (m, 2H), 7.25–7.35 (m, 5H), 5.6 (d, 2H, J=3.5 Hz), 4.15 (d, 2H, J=21.0 Hz), and 3.0 ppm (dd, 3H, J=22.0 Hz and 0.78 Hz).

Workup

  1. concentrationconcentrated
  2. additionThe residue was treated with diethyl ether
  3. concentrationthe mixture was concentrated to the precipitation point
  4. customThe solid was purified by HPLC
  5. customThe acetonitrile was evaporated
  6. extractionthe aqueous phase was extracted with ethyl acetate
  7. washwashed with water and brine
  8. customThe organic phase was evaporated to dryness
  9. customthe residue was dried for 15 hours at 91° C.

Sources & evidence

ORD record
ord-0b747c6b049e40288d0b4a711a3bcccf
Source dataset
uspto-grants-2006_06
Patent number
US07056943B2

Reaction notes

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