HCID 69549477, compound → HCID 10690878, compound

HRID 1823200Notes

Reaction equation

HRID 1823200 reaction equation
[CH3:1][CH2:2][O:3][C:4]([C@@H:6]1[CH2:10][C@@H:9]([CH2:11][CH:12]=[CH:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:8](=[O:20])[N:7]1[C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])=[O:5]>CO.[Pd]>[CH3:1][CH2:2][O:3][C:4]([C@@H:6]1[CH2:10][C@@H:9]([CH2:11][CH2:12][CH2:13][C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:8](=[O:20])[N:7]1[C:21]([O:23][C:24]([CH3:25])([CH3:27])[CH3:26])=[O:22])=[O:5]

Participants

4

Reactant 1

HCID 69549477HCID 69549477, compound

Product 1

HCID 10690878HCID 10690878, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of the compound obtained from Step A (6.0 g) and Pd/C (10%, 620 mg) in methanol (150 mL) was hydrogenated at 40 psi in a par-shaker for 3.0 h. Pd/C was removed by filtration through a pad of celite. Removal of solvent under reduced pressure gave practically pure product as a viscous oil. 1HNMR (300 MHz, CDCl3) δ 7.29–7.14 (m, 5H), 4.53 (d, J=9.5 Hz, 1H), 4.22 (q, J=7.0 Hz, 2H), 2.60 (m, 3H), 2.20 (m, 1 H), 1.98 (m, 2H), 1.64 (m, 2H), 1.50 (s, 9H), 1.28 (t, J=7.0 Hz, 3H).

Workup

  1. customPd/C was removed by filtration through a pad of celite
  2. customRemoval of solvent under reduced pressure
  3. customgave practically pure product as a viscous oil

Sources & evidence

ORD record
ord-6fc3aa54b7114520b96c19cb10babc2f
Source dataset
uspto-grants-2006_05
Patent number
US07037911B2

Reaction notes

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