Trifluoroacetic acid → HCID 11342032, compound

HRID 864527Notes

Reaction equation

HRID 864527 reaction equation
[S:1]1[CH:5]=[CH:4][C:3](/[C:6](=[CH:14]\[C:15]2[C:23]3[C:18](=[CH:19][C:20]([Cl:25])=[CH:21][C:22]=3[Cl:24])[N:17]([S:26]([C:29]3[CH:34]=[CH:33][C:32]([CH3:35])=[CH:31][CH:30]=3)(=[O:28])=[O:27])[C:16]=2[C:36]([O:38][CH2:39][CH3:40])=[O:37])/[C:7]([O:9]C(C)(C)C)=[O:8])=[CH:2]1.FC(F)(F)C(O)=O>C(OCC)(=O)C>[S:1]1[CH:5]=[CH:4][C:3](/[C:6](=[CH:14]\[C:15]2[C:23]3[C:18](=[CH:19][C:20]([Cl:25])=[CH:21][C:22]=3[Cl:24])[N:17]([S:26]([C:29]3[CH:34]=[CH:33][C:32]([CH3:35])=[CH:31][CH:30]=3)(=[O:28])=[O:27])[C:16]=2[C:36]([O:38][CH2:39][CH3:40])=[O:37])/[C:7]([OH:9])=[O:8])=[CH:2]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 11354054HCID 11354054, compound

Product 1

HCID 11342032HCID 11342032, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Combine (E)-2-(thien-3-yl)-3-(1-p-toluenesulfonyl-2-carboethoxy-4,6-dichloroindol-3-yl)propenoic acid, t-butyl ester and trifluoroacetic acid (10 mL). After 45 min, evaporate in vacuo to obtain a residue. Dissolve the residue in ethyl acetate and extract with water. Evaporate the organic layer in vacuo to obtain a residue. Triturate with pentane containing a small amount of ether to give a solid. Recrystallize the solid from cyclohexane/ethyl acetate, filter, and dry to give the title compound: mp 197°-200° C. (dec); 1H NMR (CDCl3) δ 8.00 (s, 1H), 7.95 (d, 1H, J=1.7 Hz), 7.74 (d, 2H, J=8.5 Hz), 7.27 (d, 2H, J=8.5 Hz), 7.25 (d, 1H, J=1.7 Hz), 7.08 (d, 1H, J=2.8 Hz), 7.08 (d, 1H, J=3.6 Hz), 6.81 (dd, 1H, J=3.6, 2.8 Hz), 4.22 (q, 2H, J=7.2 Hz), 2.40 (s, 3H), 1.28 (t, 3H, J=7.2 Hz); 1H NMR (DMSO-d6) δ 13.07 (br s, 1H), 7.88 (d, 1H, J=1.7 Hz), 7.74 (d, 2H, J=8.4 Hz), 7.66 (s, 1H), 7.57 (d, 1H, J=1.7 Hz), 7.44 (d, 2H, J=8.4 Hz), 7.27 (dd, 1H, J=5.0, 2.9 Hz), 7.09 (dd, 1H, J=2.9, 1.2 Hz), 6.63 (dd, 1H, J=5.0, 1.2 Hz), 4.11 (q, 2H, J=7.1 Hz), 2.36 (s, 3H), 1.14 (t, 3H, J=7.1 Hz). Elemental Analysis calculated for C25H19Cl2NO6S2 : C, 53.20; H, 3.39; N, 2.48. Found: C, 52.80; H, 3.19; N, 2.29.

Workup

  1. customevaporate in vacuo
  2. customto obtain a residue
  3. extractionextract with water
  4. customEvaporate the organic layer in vacuo
  5. customto obtain a residue
  6. customTriturate with pentane containing a small amount of ether
  7. customto give a solid
  8. customRecrystallize the solid from cyclohexane/ethyl acetate
  9. filtrationfilter
  10. customdry

Sources & evidence

ORD record
ord-efbeb996be8c47a197029e0db4ed15fa
Source dataset
uspto-grants-1996_10
Patent number
US05563157

Reaction notes

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