HCID 21980758, compound → HCID 21980912, compound

HRID 11133Notes

Reaction equation

HRID 11133 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]=1

Participants

4

Reactant 1

HCID 21980758HCID 21980758, compound

Product 1

HCID 21980912HCID 21980912, compoundYield 135%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 21899815MeOH tetrahydrofuranSolvent

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).

Workup

  1. customprepared
  2. customThe catalyst was removed by filtration through Celite
  3. washwashing through with more solvent
  4. customchromatographed on silica
  5. washElution with ethyl acetate/petroleum ether (1:1)

Sources & evidence

ORD record
ord-5fdf3bedfc814e3c8a3029fbf4e6173c
Source dataset
uspto-grants-2006_08
Patent number
US07094798B1

Reaction notes

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