Sodium Hydroxide → 2-(3-Bromo-phenoxy)-3-(4-[2-(2-cyclohexyl-5-methyl-oxazol-4-yl)-ethoxy]-phenyl}-2-methyl-propionic acid

HRID 585289Notes

Reaction equation

HRID 585289 reaction equation
[OH-].[Na+].C([O:5][C:6](=[O:39])[C:7]([O:31][C:32]1[CH:37]=[CH:36][CH:35]=[C:34]([Br:38])[CH:33]=1)([CH3:30])[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>[Br:38][C:34]1[CH:33]=[C:32]([CH:37]=[CH:36][CH:35]=1)[O:31][C:7]([CH3:30])([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:6]([OH:39])=[O:5]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 208231272-(3-Bromo-phenoxy)-3-{4-[2-(2-cyclohexyl-5-methyl-oxazol-4-yl)-ethoxy]-phenyl}-2-methyl-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 223400282-(3-Bromo-phenoxy)-3-(4-[2-(2-cyclohexyl-5-methyl-oxazol-4-yl)-ethoxy]-phenyl}-2-methyl-propionic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

5N NaOH (0.5 mL) was added to a solution of 2-(3-Bromo-phenoxy)-3-{4-[2-(2-cyclohexyl-5-methyl-oxazol-4-yl)-ethoxy]-phenyl}-2-methyl-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 7.17 (m, 5H), 6.90-6.76 (m, 3H), 4.12 (t, 2H, J=6.26 Hz), 3.22 (d, 1H, J=13.69 Hz), 3.10 (d, 1H, J=13.69 Hz), 2.95 (t, 2H, J=6.26 Hz), 2.90-2.68 (m, 1H), 2.30 (s, 3H), 2.01 (d, 2H, J=13.30 Hz), 1.79 (d, 2H, J=12.90 Hz), 1.69 (d, 1H, J=13.30 Hz), 1.40 (s, 3H), 1.58-1.21 (m, 4H). MS [EI+] 543 (M+H)+.

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-c8174325cc2143728d6c242067347cdc
Source dataset
uspto-grants-2005_08
Patent number
US06930120B2

Reaction notes

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