HCID 86725329, compound → HCID 86725328, compound

HRID 925215Notes

Reaction equation

HRID 925215 reaction equation
[CH2:1]([O:3][C:4]([N:6]1[CH2:23][CH2:22][C:10]2[C:11]3[C:12](=[CH:20][CH3:21])[C:13]([F:19])([F:18])[CH2:14][C:15]=3[CH:16]=[CH:17][C:9]=2[CH2:8][CH2:7]1)=[O:5])[CH3:2]>CCO>[CH2:1]([O:3][C:4]([N:6]1[CH2:23][CH2:22][C:10]2[C:11]3[CH:12]([CH2:20][CH3:21])[C:13]([F:19])([F:18])[CH2:14][C:15]=3[CH:16]=[CH:17][C:9]=2[CH2:8][CH2:7]1)=[O:5])[CH3:2]

Participants

3

Reactant 1

HCID 86725329HCID 86725329, compound

Product 1

HCID 86725328HCID 86725328, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Into a 100 ml flask, the product from step (a) dissolved in EtOH (20 ml) was added. The flask was purged with Ar and 10% Pd—C (15 mg) was added. The reaction was stirred over hydrogen (atmospheric pressure) for 16 hours. The reaction mixture was filtered through celite and the solvent evaporated in vacuo. The crude residue was purified by silica-gel chromatography (gradient elution: 0 to 20% EtOAc in hexanes) to give the sub-title product as a colorless oil (42 mg). 1H NMR (300 MHz, CDCl3) δ 7.02-6.96 (m, 2H); 4.17 (q, J=7.2 Hz, 2H); 3.65-3.56 (m, 4H); 3.49-3.21 (m, 3H) 2.89-2.83 (m, 4H); 1.76-1.56 (m, 2H); 1.28 (t, J=6.9 Hz, 3H); 0.94 (t, J=7.5 Hz, 3H); MS: ESI (positive): 324 (M+1).

Workup

  1. additionwas added
  2. customThe flask was purged with Ar and 10% Pd—C (15 mg)
  3. additionwas added
  4. filtrationThe reaction mixture was filtered through celite
  5. customthe solvent evaporated in vacuo
  6. customThe crude residue was purified by silica-gel chromatography (gradient elution: 0 to 20% EtOAc in hexanes)

Sources & evidence

ORD record
ord-eab81430caf549278d485a518103b423
Source dataset
uspto-grants-2016_03
Patent number
US09284277B2

Reaction notes

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