HCID 23590030, compound → HCID 135617795, compound

HRID 1609938Notes

Reaction equation

HRID 1609938 reaction equation
[CH2:1]([O:3][C:4](=[O:38])[C:5]([O:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:16][CH2:17][C:18]2[N:19]=[C:20]([C:24]3[CH:29]=[CH:28][C:27]([O:30]CC4C=CC=CC=4)=[CH:26][CH:25]=3)[O:21][C:22]=2[CH3:23])=[CH:11][CH:10]=1)([CH3:7])[CH3:6])[CH3:2]>[Pd].O1CCCC1.CO.CCOC(C)=O>[CH2:1]([O:3][C:4](=[O:38])[C:5]([O:8][C:9]1[CH:10]=[CH:11][C:12]([O:15][CH2:16][CH2:17][C:18]2[N:19]=[C:20]([C:24]3[CH:29]=[CH:28][C:27]([OH:30])=[CH:26][CH:25]=3)[O:21][C:22]=2[CH3:23])=[CH:13][CH:14]=1)([CH3:7])[CH3:6])[CH3:2]

Participants

6

Reactant 1

HCID 23590030HCID 23590030, compound

Product 1

HCID 135617795HCID 135617795, compoundYield 95.2%

Reagents, catalysts & solvents 4

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 2-(4-{2-[2-(4-benzyloxy-phenyl)-5-methyl-oxazol-4-yl]-ethoxy}-phenoxy)-2-methyl-propionic acid ethyl ester (8.16 g, 15.8 mmol) and 5% palladium on carbon (1.63 g) in tetrahydrofuran (100 mL) and methanol (100 mL) was purged successively with nitrogen then hydrogen, and then stirred under a hydrogen balloon at room temperature for 18 h. The reaction mixture was filtered through hyflo and solvent was removed from the filtrate in vacuo to give an oil which was dissolved in EtOAc and dried (MgSO4). The solvent was removed in vacuo to afford 6.40 g (95%) of 2-(4-{2-[2-(4-hydroxy-phenyl)-5-methyl-oxazol-4-yl]-ethoxy}-phenoxy)-2-methyl-propionic acid ethyl ester. 1H NMR (500 MHz, CDCl3) δ 8.25 (bs, 1H), 7.32 (d, 2H, J=8.79 Hz), 6.75-6.67 (m, 4H), 6.65 (d, 2H, J=8.79 Hz), 4.17 (q, 2H, J=6.84 Hz), 4.09 (t, 2H, J=6.35 Hz), 2.88 (t, 2H, J=6.35 Hz), 2.30 (s, 3H), 1.45 (s, 6H), 1.21 (t, 3H, J=6.84 Hz); 13C (125 MHz, CDCl3) δ 174.4, 160.2, 159.0, 154.3, 148.9, 144.7, 131.5, 128.1, 122.0, 121.6, 118.7, 115.9, 115.7, 114.9, 79.8, 66.8, 61.3, 25.9, 25.2, 14.1, 10.1; IR (KBr) 2985, 2941, 2809, 2606, 1742, 1731, 1507, 1442, 1277, 1233, 1213, 1170, 1137 cm−1; UV (EtOH) λmax 285 nm (ε 21145), 219 nm (•15842); HRMS (ES+) m/z exact mass calcd for C24H28NO6 426.1917, found 426.1896; Anal. Calc'd for C24H27NO6: C, 67.75; H, 6.40; N, 3.29. Found C, 67.22; H, 6.50; N, 2.79

Workup

  1. customwas purged successively with nitrogen
  2. filtrationThe reaction mixture was filtered through hyflo and solvent
  3. customwas removed from the filtrate in vacuo
  4. customto give an oil which
  5. dry with materialdried (MgSO4)
  6. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-7de48fd0620742e5b1d3bde8bd88aa9b
Source dataset
uspto-grants-2006_01
Patent number
US06982278B2

Reaction notes

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