Potassium Carbonate → HCID 10188807, compound

HRID 348314Notes

Reaction equation

HRID 348314 reaction equation
C([O:3][C:4](=[O:26])[C:5]([O:15][C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([C:22]([CH3:25])([CH3:24])[CH3:23])[CH:17]=1)([CH3:14])[CH2:6][C:7]1[CH:12]=[CH:11][C:10](O)=[CH:9][CH:8]=1)C.[CH3:27][C:28]1[O:32][C:31]([C:33]2[CH:38]=[CH:37][C:36]([C:39]3[S:40][CH:41]=[CH:42][CH:43]=3)=[CH:35][CH:34]=2)=[N:30][C:29]=1[CH2:44][CH2:45][O:46]S(C1C(C)=CC=CC=1)(=O)=O.C([O-])([O-])=O.[K+].[K+].[OH-].[Na+]>C(O)C>[C:22]([C:18]1[CH:17]=[C:16]([CH:21]=[CH:20][CH:19]=1)[O:15][C:5]([CH3:14])([CH2:6][C:7]1[CH:8]=[CH:9][C:10]([O:46][CH2:45][CH2:44][C:29]2[N:30]=[C:31]([C:33]3[CH:34]=[CH:35][C:36]([C:39]4[S:40][CH:41]=[CH:42][CH:43]=4)=[CH:37][CH:38]=3)[O:32][C:28]=2[CH3:27])=[CH:11][CH:12]=1)[C:4]([OH:26])=[O:3])([CH3:25])([CH3:23])[CH3:24]

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 69317602HCID 69317602, compoundHCID 86593520HCID 86593520, compound

Product 1

HCID 10188807HCID 10188807, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A mixture of 2-(3-tert-butyl-phenoxy)-3-(4-hydroxyphenyl)-2-methylpropionic acid ethyl ester (0.030 mmol) (see Ex. 23, Part B), toluenesulfonic acid 2-(5-methyl-2-(4-thiophen-2-yl-phenyl)-oxazol-4-yl)ethyl ester (0.030 mmol) (see Ex. 3, Part B) and 325 mesh K2CO3 (0.084 g, 0.60 mmol) in ethanol (2 mL) was heated to reflux for 24 h under N2. Aqueous 5N NaOH (0.5 mL) and additional ethanol (1 mL) was added to the reaction mixture and it was heated at reflux for an additional 2 h. The reaction was cooled and the solvent removed in vacuo. The residue was acidified with aqueous 1 N HCl (5 mL), extracted with water and CH2Cl2 and the organic layer dried by passing it through a Varian Chem Elut 1003 cartridge. The solvent was removed in vacuo to give 2-(3-tert-butyl-phenoxy)-2-methyl-3-(4-{2-[5-methyl-2-(4-thiophen-2-yl-phenyl)-oxazol-4-yl]-ethoxy)-phenyl)-propionic acid. 1H NMR (400 MHz, CDCl3) δ 7.97 (d, 2H, J=8.60 Hz), 7.67 (d, 2H, J=8.60 Hz), 7.36 (dd, 1H, J=3.91 Hz, 1.17 Hz), 7.33 (dd, 1H, J=3.91 Hz, 1.17 Hz), 7.20–7.16 (m, 3H), 7.12–7.07 (m, 2H), 6.89 (t, 1H, J=1.96 Hz), 6.84 (d, 2H, J=8.60 Hz), 6.72 (dd, 1H, J=8.60 Hz, 2.74 Hz), 4.22 (t, 2H, J=6.65 Hz), 3.25 (d, 1H, J=14.08 Hz), 3.15 (d, 1H, J=14.08 Hz), 3.01 (t, 2H, J=6.65 Hz), 2.40 (s, 3H), 1.43 (s, 3H), 1.26 (s, 9H). HRMS (ES+) m/z exact mass calcd for C36H38NO5S 596.2471, found 596.2454.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 24 h under N2
  3. temperaturewas heated
  4. temperatureat reflux for an additional 2 h
  5. temperatureThe reaction was cooled
  6. customthe solvent removed in vacuo
  7. extractionextracted with water and CH2Cl2
  8. customthe organic layer dried
  9. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-6f03c69d47de4185b6683763fe2ce5d8
Source dataset
uspto-grants-2007_02
Patent number
US07176224B2

Reaction notes

Loading…