HCID 52943823, compound → HCID 135979913, compound

HRID 1594019Notes

Reaction equation

HRID 1594019 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:7]([C:41]([O:43][CH2:44][CH3:45])=[O:42])=[C:8]([C:27]2[CH:32]=[CH:31][C:30]([O:33]CC3C=CC=CC=3)=[CH:29][CH:28]=2)[N:9]2[C:14]=1[C:13]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[CH:12][C:11]([N:21]1[CH2:26][CH2:25][O:24][CH2:23][CH2:22]1)=[N:10]2)=[O:5])[CH3:2]>CCO.[Pd]>[CH2:1]([O:3][C:4]([C:6]1[C:7]([C:41]([O:43][CH2:44][CH3:45])=[O:42])=[C:8]([C:27]2[CH:28]=[CH:29][C:30]([OH:33])=[CH:31][CH:32]=2)[N:9]2[C:14]=1[C:13]([C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)=[CH:12][C:11]([N:21]1[CH2:22][CH2:23][O:24][CH2:25][CH2:26]1)=[N:10]2)=[O:5])[CH3:2]

Participants

4

Reactant 1

HCID 52943823HCID 52943823, compound

Product 1

HCID 135979913HCID 135979913, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

10% Pd/C was added to a solution of 37 in 95% EtOH (20 mL). The reaction mixture was stirred at ambient temperature under a H2 atmosphere for 24 h. The reaction mixture was filtered through celite and the filtrate was concentrated in vacuo. The resulting residue was triturated in 1:1 Et2O/hexane and the precipitate was collected by vacuum filtration to provide the title compound as an off-white solid. 1H NMR (DMSO-d6) δ 0.85 (t, J=7.1 Hz, 3H), 1.07 (t, J=7.1 Hz, 3H), 3.38 (m, 4H), 3.51 (q, J=7.2 Hz, 2H), 3.66 (m, 4H), 4.06 (q, J=7.1 Hz, 2H), 6.83 (m, 3H), 7.40-7.49 (m, 7H), 9.67 (s, 1H). Mass Spectrum (ESI+) m/e=516.3 (M+H).

Workup

  1. filtrationThe reaction mixture was filtered through celite
  2. concentrationthe filtrate was concentrated in vacuo
  3. customThe resulting residue was triturated in 1:1 Et2O/hexane
  4. filtrationthe precipitate was collected by vacuum filtration

Sources & evidence

ORD record
ord-75432081be9f4c4594de1f581d1c2ebf
Source dataset
uspto-grants-2007_11
Patent number
US07300932B2

Reaction notes

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