HCID 69817590, compound → HCID 18924840, compound

HRID 1288827Notes

Reaction equation

HRID 1288827 reaction equation
[CH2:1]([C:3]1([CH2:48][CH3:49])[C:6](=[O:7])[N:5]([C:8]([NH:10][CH:11]([C:15]2[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=2)[CH2:12][CH2:13][CH3:14])=[O:9])[CH:4]1[O:22][C:23]1[CH:28]=[CH:27][C:26]([C:29]([NH:31][CH2:32][CH2:33][N:34]2[CH2:39][CH2:38][CH:37]([O:40]CC3C=CC=CC=3)[CH2:36][CH2:35]2)=[O:30])=[CH:25][CH:24]=1)[CH3:2]>C(O)(=O)C.[Pd]>[CH2:48]([C:3]1([CH2:1][CH3:2])[C:6](=[O:7])[N:5]([C:8]([NH:10][CH:11]([C:15]2[CH:16]=[CH:17][C:18]([CH3:21])=[CH:19][CH:20]=2)[CH2:12][CH2:13][CH3:14])=[O:9])[CH:4]1[O:22][C:23]1[CH:24]=[CH:25][C:26]([C:29]([NH:31][CH2:32][CH2:33][N:34]2[CH2:35][CH2:36][CH:37]([OH:40])[CH2:38][CH2:39]2)=[O:30])=[CH:27][CH:28]=1)[CH3:49]

Participants

4

Reactant 1

HCID 69817590HCID 69817590, compound

Product 1

HCID 18924840HCID 18924840, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

A solution of the amide from step A above in 10 ml of glacial acetic acid containing 22 mg of 10% Pd/C is hydrogenated under 42 lb hydrogen pressure. When TLC indicate completion of the reaction, the mixture is filtered and concentrated in vacuo after the addition of 50 ml toluene. The residue is dissolved in ethyl acetate, washed with saturated sodium bicarbonate solution. The organic layer is dried with sodium sulfate and concentrated in vacuo. The residue is chromatographed on 15 g silica gel using 5% methanol in methylene chloride and yields 96 mg of

Workup

  1. customcompletion of the reaction
  2. filtrationthe mixture is filtered
  3. concentrationconcentrated in vacuo
  4. additionafter the addition of 50 ml toluene
  5. dissolutionThe residue is dissolved in ethyl acetate
  6. washwashed with saturated sodium bicarbonate solution
  7. dry with materialThe organic layer is dried with sodium sulfate
  8. concentrationconcentrated in vacuo
  9. customThe residue is chromatographed on 15 g silica gel using 5% methanol in methylene chloride
  10. customyields 96 mg of

Sources & evidence

ORD record
ord-31d4987a8188412cbe2fd6fdf2bd1d26
Source dataset
uspto-grants-1998_05
Patent number
US05747485

Reaction notes

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