Potassium Carbonate → HCID 10301033, compound

HRID 1393507Notes

Reaction equation

HRID 1393507 reaction equation
[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:4][C:3]=1[CH2:13][CH2:14][O:15]S(C1C=CC(C)=CC=1)(=O)=O.C([O:28][C:29](=[O:51])[C:30]([CH3:50])([O:39][C:40]1[CH:41]=[C:42]2[C:47](=[CH:48][CH:49]=1)[N:46]=[CH:45][CH:44]=[CH:43]2)[CH2:31][C:32]1[CH:37]=[CH:36][C:35](O)=[CH:34][CH:33]=1)C.C([O-])([O-])=O.[K+].[K+].[OH-].[Na+]>CCO>[CH3:50][C:30]([O:39][C:40]1[CH:41]=[C:42]2[C:47](=[CH:48][CH:49]=1)[N:46]=[CH:45][CH:44]=[CH:43]2)([CH2:31][C:32]1[CH:33]=[CH:34][C:35]([O:15][CH2:14][CH2:13][C:3]2[N:4]=[C:5]([C:7]3[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=3)[O:6][C:2]=2[CH3:1])=[CH:36][CH:37]=1)[C:29]([OH:51])=[O:28]

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 120517392-(5-Methyl-2-phenyloxazol-4-yl)ethyl 4-methylbenzenesulfonateHCID 20823157HCID 20823157, compound

Product 1

HCID 10301033HCID 10301033, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of toluene-4-sulfonic acid 2-(5-methyl-2-phenyl-oxazol-4-yl)-ethyl ester (94 mg, 0.26 mmol), 3-(4-Hydroxy-phenyl)-2-methyl-2-(quinolin-6-yloxy)-propionic acid ethyl ester (77.3 mg, 0.22 mmol) and K2CO3 (61 mg, 0.44 mmol) in 2 mL of EtOH was heated to 80° C. for overnight. Then 5N NaOH (0.26 mL, 1.3 mmol) was added and reaction mixture was stand at same temperature for 2 h. The mixture was cooled off to r.t. and organic solvent was removed under vacuum. Residue was then dissolved in CH2Cl2 and 1N HCl. Aqueous layer was washed with CH2Cl2 (2×). Combined organic layer was washed with brine, dried over Na2SO4, filtered and concentrated. Residue was purified by MS/LC to give title compound as white solid (55.6 mg, 50%). 1H NMR (400 MHz, CDCl3) δδ8.76 (d, 1H, J=4.4 Hz), 8.28 (d, 1H, J=8.4 Hz), 7.94 (d, 1H, J=9.2 Hz), 7.89-7.87 (m, 2H), 7.51-7.45 (m, 3H), 7.38-7.32 (m, 2H), 7.25-7.23 (m, 1H), 7.20 (d, 1H, J=2.4 Hz), 7.16 (d, 2H, J=8.8 Hz), 6.85 (d, 2H, J=8.8 Hz), 4.17 (t, 2H, J=6.6 Hz), 3.29, 3.11 (ABq, 2H, J=13.4 Hz), 2.90 (t, 2H, J=6.6 Hz), 2.33 (s, 3H), 1.42 (s, 3H). HRMS (ES4) m/z exact mass calcd for C31H29N2O5 (m+1) 509.2076, found 509.2095.

Workup

  1. customreaction mixture
  2. customfor 2 h
  3. customorganic solvent was removed under vacuum
  4. dissolutionResidue was then dissolved in CH2Cl2
  5. washAqueous layer was washed with CH2Cl2 (2×)
  6. washCombined organic layer was washed with brine
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customResidue was purified by MS/LC

Sources & evidence

ORD record
ord-cfbac460562849cba1d97da0dc96b7a6
Source dataset
uspto-grants-2008_03
Patent number
US07345070B2

Reaction notes

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