Potassium Carbonate → HCID 10279373, compound

HRID 1393508Notes

Reaction equation

HRID 1393508 reaction equation
[CH:1]1([C:7]2[O:8][C:9]([CH3:25])=[C:10]([CH2:12][CH2:13][O:14]S(C3C=CC(C)=CC=3)(=O)=O)[N:11]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.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>[CH:1]1([C:7]2[O:8][C:9]([CH3:25])=[C:10]([CH2:12][CH2:13][O:14][C:35]3[CH:34]=[CH:33][C:32]([CH2:31][C:30]([CH3:50])([O:39][C:40]4[CH:41]=[C:42]5[C:47](=[CH:48][CH:49]=4)[N:46]=[CH:45][CH:44]=[CH:43]5)[C:29]([OH:51])=[O:28])=[CH:37][CH:36]=3)[N:11]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 20823157HCID 20823157, compoundHCID 22340021Toluene-4-sulfonic acid 2-(2-cyclohexyl-5-methyloxazol-4-yl)-ethyl ester

Product 1

HCID 10279373HCID 10279373, compoundYield 48.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of Toluene-4-sulfonic acid 2-(2-cyclohexyl-5-methyl-oxazol-4-yl)-ethyl ester (96 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 (54.5 mg, 48%). 1H NMR (400 MHz, CDCl3) δδ8.74 (dd, 1H, J=4.0, 1.6 Hz), 8.24 (d, 1H, J=6.8 Hz), 7.92 (d, 1H, J=9.2 Hz), 7.45 (dd, 1H, J=8.2, 4.2 Hz), 7.33 (dd, 1H, J=5.2, 2.8 Hz), 7.19 (d, 1H, J=2.8 Hz), 7.15, 6.82 (ABq, 4H, J=8.6 Hz), 4.08 (t, 2H, J=6.8 Hz), 3.29, 3.11 (ABq, 2H, J=13.8 Hz), 2.76 (t, 2H, J=6.8 Hz), 2.68-2.63 (m, 1H), 2.18 (s, 3H), 1.93-1.87 (m, 2H), 1.71-1.65 (m, 2H), 1.62-1.57 (m, 1H), 1.46-1.14 (m, 5H), 1.42 (s, 3H). HRMS (ES+) m/z exact mass calcd for C31H35N2O5 (m+1) 515.2546, found 515.2567.

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-9303f558548f4d3caeb58062a12e2ff1
Source dataset
uspto-grants-2008_03
Patent number
US07345070B2

Reaction notes

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