Sodium Hydroxide → 3-{4-[2-(2-Cyclohexyl-5-methyl-oxazol-4-yl)-ethoxy]-phenyl}-2-methyl-2-(3-thiophen-3-yl-phenoxy)-propionic Acid

HRID 585291Notes

Reaction equation

HRID 585291 reaction equation
[OH-].[Na+].C([O:5][C:6](=[O:43])[C:7]([CH3:42])([O:30][C:31]1[CH:36]=[CH:35][CH:34]=[C:33]([C:37]2[CH:41]=[CH:40][S:39][CH:38]=2)[CH:32]=1)[CH2:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:16][CH2:17][C:18]2[N:19]=[C:20]([CH:24]3[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]3)[O:21][C:22]=2[CH3:23])=[CH:11][CH:10]=1)C.C(OC(=O)C(C)(OC1C=CC=CC=1)CC1C=CC(OCCC2N=C(C3CCCCC3)OC=2C)=CC=1)C>C(O)C>[CH:24]1([C:20]2[O:21][C:22]([CH3:23])=[C:18]([CH2:17][CH2:16][O:15][C:12]3[CH:11]=[CH:10][C:9]([CH2:8][C:7]([CH3:42])([O:30][C:31]4[CH:36]=[CH:35][CH:34]=[C:33]([C:37]5[CH:41]=[CH:40][S:39][CH:38]=5)[CH:32]=4)[C:6]([OH:43])=[O:5])=[CH:14][CH:13]=3)[N:19]=2)[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 208231423-(4-[2-(2-Cyclohexyl-5-methyl-oxazol-4-yl)-ethoxy]-phenyl}-2-methyl-2-(3-thiophen-3-yl-phenoxy)-propionic acid ethyl esterHCID 208231432-Methyl-3-(4-{2-[5-methyl-2-cyclohexyl-oxazol-4-yl]-ethoxy}-phenyl)-2-phenoxypropionic Acid Ethyl Ester

Product 1

HCID 223399763-{4-[2-(2-Cyclohexyl-5-methyl-oxazol-4-yl)-ethoxy]-phenyl}-2-methyl-2-(3-thiophen-3-yl-phenoxy)-propionic Acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

5N NaOH (0.5 mL) was added to a solution of 3-{4-[2-(2-Cyclohexyl-5-methyl-oxazol-4-yl)-ethoxy]-phenyl}-2-methyl-2-(3-thiophen-3-yl-phenoxy)-propionic acid ethyl ester and 3-{4-[2-(2-Cyclohexyl-5-methyl-oxazol-4-yl)-ethoxy-]-phenyl}-2-methyl-2-phenoxy-propionic acid ethyl ester in ethanol (4 mL). The resultant mixture was refluxed under an atmosphere of nitrogen for 2 h, then cooled to ambient temperature. The reaction mixture was concentrated in vacuo, diluted with 1N HCl, and extracted with CH2Cl2. The organic layer was dried through a Varian ChemElut cartridge, concentrated in vacuo, and purified by LCMS. 1H NMR (400 MHz, CDCl3): δ 7.39-7.26 (m, 5H), 7.17 (d, 2H, J=8.60 Hz), 7.11-7.10 (m, 1H), 6.82-6.80 (m, 1H), 6.78 (d, 2H, J=8.60 Hz), 4.11 (t, 2H, J=6.26 Hz), 3.25 (d, 1H, J=14.08 Hz), 3.13 (d, 1H, J=14.08 Hz), 2.93 (t, 2H, J=6.26 Hz), 2.87-2.81 (m, 1H), 2.28 (s, 3H), 1.99 (d, 2H, J=12.51 Hz), 1.77 (d, 2H, J=12.51), 1.67 (d, 2H, J=12.51), 1.57-1.46 (m, 2H), 1.45 (s, 3H), 1.37-1.19 (m, 2H). MS [ES+] m/z exact mass calcd for C32H36NO5S 546.2314, found 546.2308.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. additiondiluted with 1N HCl
  3. extractionextracted with CH2Cl2
  4. customThe organic layer was dried through a Varian ChemElut cartridge
  5. concentrationconcentrated in vacuo
  6. custompurified by LCMS

Sources & evidence

ORD record
ord-6bda5e6263014371b7c18909d7870502
Source dataset
uspto-grants-2005_08
Patent number
US06930120B2

Reaction notes

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