HCID 58820555, compound → HCID 69742616, compound

HRID 458465Notes

Reaction equation

HRID 458465 reaction equation
C([O:8][C:9]([C:11]1[CH:16]=[CH:15][C:14]([C:17]2[C:25]([C:26]([O:28][CH2:29][CH3:30])=[O:27])=[C:24]([CH2:31][CH2:32][C:33]3[CH:38]=[CH:37][C:36]([F:39])=[CH:35][CH:34]=3)[CH:23]=[C:22]3[C:18]=2[C:19](=[O:43])[N:20]2[CH2:42][CH2:41][CH2:40][C@H:21]23)=[CH:13][CH:12]=1)=[O:10])C1C=CC=CC=1>C(OCC)(=O)C.[Pd]>[CH2:29]([O:28][C:26]([C:25]1[C:17]([C:14]2[CH:13]=[CH:12][C:11]([C:9]([OH:10])=[O:8])=[CH:16][CH:15]=2)=[C:18]2[C:22](=[CH:23][C:24]=1[CH2:31][CH2:32][C:33]1[CH:34]=[CH:35][C:36]([F:39])=[CH:37][CH:38]=1)[C@@H:21]1[CH2:40][CH2:41][CH2:42][N:20]1[C:19]2=[O:43])=[O:27])[CH3:30]

Participants

4

Reactant 1

HCID 58820555HCID 58820555, compound

Product 1

HCID 69742616HCID 69742616, compoundYield 98%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of Example 48 (300 mg, 0.51 mmol) in ethyl acetate (25 ml) was added 10% Pd/C (10% w/w, 30 mg) and was stirred under H2 (1 atms.) for 18 hr. The Pd/C filtered through celite (1 g) and the filtrate concentrated to provide title compound as a white solid (243 mg, 0.50 mmol). 1H NMR (400 MHz, CDCl3) δ 8.07 (d, J=8.4 Hz, 2H), 7.49–7.42 (m, 2H), 7.13 (s, 1H), 7.09–7.06 (m, 2H), 6.96–6.92 (m, 2H), 4.62–4.58 (m, 1H), 3.94 (q, 2H), 3.68–3.61 (m, 1H), 3.33–3.29 (m, 1H), 3.02–2.87 (m, 4H), 2.32–2.03 (m, 3H), 1.24–1.19 (m, 1H), 0.86 (t, 3H) ppm. ESI-MS m/z 488 (M+H)+. HPLC (93%).

Workup

  1. filtrationThe Pd/C filtered through celite (1 g)
  2. concentrationthe filtrate concentrated

Sources & evidence

ORD record
ord-c5429b222a364ded8e2c7ce6bb1731b4
Source dataset
uspto-grants-2007_03
Patent number
US07189851B2

Reaction notes

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