HCID 86718365, compound → HCID 86718366, compound

HRID 1518759Notes

Reaction equation

HRID 1518759 reaction equation
[CH2:1]([O:3][C:4](=[O:24])[CH:5]=[CH:6][C@@H:7]([CH3:23])[C@H:8]([N:14]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH3:15])[C:9]1[O:10][CH:11]=[CH:12][CH:13]=1)[CH3:2]>C(OCC)(=O)C.[Pd]>[CH2:1]([O:3][C:4](=[O:24])[CH2:5][CH2:6][C@@H:7]([CH3:23])[C@H:8]([N:14]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH3:15])[C:9]1[O:10][CH:11]=[CH:12][CH:13]=1)[CH3:2]

Participants

4

Reactant 1

HCID 86718365HCID 86718365, compound

Product 1

HCID 86718366HCID 86718366, compoundYield 99.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2.12c (360 mg, 1.07 mmol) in ethyl acetate (5 mL) was added Pd/C (5% on charcoal, 114 mg, 0.107 mmol) and the resulting mixture was stirred under 1 atm of H2 for 1 hour. The solid was then removed by filtration and the filtrate was concentrated in vacuo to afford 2.12d (360 mg) which was used in the next step without further purification. MS m/z (M+23) 362.3. 1H NMR (400 MHz, CDCl3) δ ppm 0.91-0.97 (m, 3H) 1.24 (t, J=7.16 Hz, 3H) 1.36-1.47 (m, 7H) 1.47-1.52 (m, 5H) 1.52-1.57 (m, 4H) 2.66 (s, 3H) 4.10 (d, J=7.24 Hz, 2H) 6.31 (d, J=1.91 Hz, 2H) 6.32 (s, 1H) 7.26 (s, 3H) 7.35 (ddd, J=1.23, 0.78, 0.67 Hz, 1H).

Workup

  1. customThe solid was then removed by filtration
  2. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-b4986f336ef9498db1f341be0d05236d
Source dataset
uspto-grants-2015_07
Patent number
US09072696B2

Reaction notes

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