HCID 22261102, compound → HCID 135550701, compound

HRID 1609939Notes

Reaction equation

HRID 1609939 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[O:16][C:17]([CH3:36])=[C:18]([CH2:20][CH2:21][O:22][C:23]3[CH:35]=[CH:34][C:26]([O:27][C:28]([CH3:33])([CH3:32])[C:29]([OH:31])=[O:30])=[CH:25][CH:24]=3)[N:19]=2)=[CH:11][CH:10]=1)C1C=CC=CC=1>[Pd].O1CCCC1.CO.C(Cl)Cl>[OH:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[O:16][C:17]([CH3:36])=[C:18]([CH2:20][CH2:21][O:22][C:23]3[CH:35]=[CH:34][C:26]([O:27][C:28]([CH3:32])([CH3:33])[C:29]([OH:31])=[O:30])=[CH:25][CH:24]=3)[N:19]=2)=[CH:11][CH:10]=1

Participants

6

Reactant 1

HCID 22261102HCID 22261102, compound

Product 1

HCID 135550701HCID 135550701, compoundYield 37%

Reagents, catalysts & solvents 4

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 2-(4-{2-[2-(4-benzyloxy-phenyl)-5-methyl-oxazol-4-yl]-ethoxy}-phenoxy)-2-methyl-propionic acid (0.238 g, 0.490 mmol) and 5% palladium on carbon (0.10 g) in tetrahydrofuran (10 mL) and methanol (10 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 CH2Cl2 and dried (MgSO4). The solvent was removed in vacuo to give a crude oil which was purified by flash chromatography (9/1 CH2Cl2/MeOH) to afford 0.072 g (37%) 2-(4-{2-[2-(4-hydroxy-phenyl)-5-methyl-oxazol-4-yl]-ethoxy}-phenoxy)-2-methyl-propionic acid. 1H NMR (500 MHz, DMSO-d6) δ 10.08 (bs, 1H), 7.70 (d, 2H, J=8.60 Hz), 6.84-6.72 (m, 6H), 4.08 (t, 2H, J=6.65 Hz), 2.83 (t, 2H, J=6.65 Hz), 2.28 (s, 3H), 1.33 (s, 6H); MS (ES+) Calc'd for C22H23NO6: Found m/e 398 (M+1, 100%)

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
  7. customto give a crude oil which
  8. customwas purified by flash chromatography (9/1 CH2Cl2/MeOH)

Sources & evidence

ORD record
ord-a8a61f23395647b7805d5360d33620c2
Source dataset
uspto-grants-2006_01
Patent number
US06982278B2

Reaction notes

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