HCID 21980758, compound → HCID 21980912, compound
Reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:20]2[C:21](=[O:25])[NH:22][C:23](=[O:24])[C:19]=2[C:18]2[C:17]3[CH:16]=[C:15]([O:26][CH3:27])[C:14](/[CH:28]=[CH:29]/[CH2:30][CH2:31][OH:32])=[CH:13][C:12]=3[NH:11][C:10]=2[CH:9]=1>O=[Pt]=O.O1CCCC1.CO>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:20]2[C:21](=[O:25])[NH:22][C:23](=[O:24])[C:19]=2[C:18]2[C:17]3[CH:16]=[C:15]([O:26][CH3:27])[C:14]([CH2:28][CH2:29][CH2:30][CH2:31][OH:32])=[CH:13][C:12]=3[NH:11][C:10]=2[CH:9]=1Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
A mixture of (170) (0.15 g, 0.33 mmol) prepared as described in example 309 and PtO2 (20 mg) in 1:1 tetrahydrofuran/methanol (30 mL) was shaken under an atmosphere of hydrogen gas at 40 psi pressure for 30 min. The catalyst was removed by filtration through Celite, washing through with more solvent. The combined filtrates were worked up and chromatographed on silica. Elution with ethyl acetate/petroleum ether (1:1) gave (171) as an orange solid (0.20 g, 100%), mp 256–260° C. (dec). 1H NMR δ [(CD3)2SO] 11.90 (br, 1H), 11.10 (br, 1H), 8.34 (s, 1H), 7.64–7.40 (m, 6H), 4.37 (br, 1H), 3.93 (s, 3H), 3.43 (t, J=6.3 Hz, 2H), 2.76 (t, J=7.6 Hz, 2H), 1.66 (m, 1H), 1.50 (m, 2H).