HCID 86747052, compound → HCID 44301977, compound

HRID 484467Notes

Reaction equation

HRID 484467 reaction equation
[C:1]1([NH:7][C:8]([CH2:10][C@@H:11]2[C:20]3[C:15](=[CH:16][C:17]([Cl:22])=[CH:18][C:19]=3[Cl:21])[NH:14][C@@H:13]([C:23]([O:25]C(C)(C)C)=[O:24])[CH2:12]2)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>FC(F)(F)C(O)=O>[C:23]([C@H:13]1[CH2:12][C@H:11]([CH2:10][C:8]([NH:7][C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)=[O:9])[C:20]2[C:15](=[CH:16][C:17]([Cl:22])=[CH:18][C:19]=2[Cl:21])[NH:14]1)([OH:25])=[O:24]

Participants

3

Reactant 1

HCID 86747052HCID 86747052, compound

Product 1

HCID 44301977HCID 44301977, compoundYield 33.5%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

Trans-4-phenylaminocarbonylmethyl-2-tertiarybutyloxycarbonyl-5,7-dichloro-1,2,3,4-tetrahydroquinoline (0.12 g) was dissolved in 10% aqueous trifluoroacetic acid (30 ml) and stood at room temperature for 30 mins. The solvents were removed under vacuum and the residue chromatographed on silica gel using 3% methanol, 1% acetic acid, 96% dichloromethane to give a solid which was recrystallised from diethyl ether/hexane to give the title compound as a colourless solid (0.035 g, m.p. 208° C. dec); δ (360 MHz, DMSO) 1.62 (1H, ddd, J=13.0, 12.4 and 3.9 Hz, CHACHBHCCHD), 2.19 (1H, d, J=13.0 Hz, CHACHBHCCHD), 2.49 (2H, m, CHEHFCONHPh), 3.58 (1H, m, CHACHBHCCHD), 4.08 (1H, dd, J=12.4 and 3.4 Hz, CHACHBHCCHD), 6.62 (2H, m, 6-H or 8-H and NH), 6.80 (1H, d, J=2.0 Hz, 6-H or 8-H), 7.04 (1H, t, J=7.4 Hz, p proton), 7.31 (2H, t, J=7.4 Hz, m protons), 7.59 (2H, d, J=7.4 Hz, o protons); m/e (FAB) 379 (M+1); Found C, 57.18; H, 4.31; N, 7.22. C18H16Cl2N2O3 requires C, 57.01; H, 4.25; N, 7.39%.

Workup

  1. customThe solvents were removed under vacuum
  2. customthe residue chromatographed on silica gel using 3% methanol, 1% acetic acid, 96% dichloromethane
  3. customto give a solid which
  4. customwas recrystallised from diethyl ether/hexane

Sources & evidence

ORD record
ord-d701d96be3a6429b9793a783b49c2577
Source dataset
uspto-grants-1993_07
Patent number
US05231102

Reaction notes

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