Sodium Hydroxide → 2-(Biphenyl-3-yloxy)-3-{4-[2-(2-cyclohexyl-5-methyl-oxazol-4-yl)-ethoxy]-phenyl)-2-methyl-propionic acid

HRID 1393502Notes

Reaction equation

HRID 1393502 reaction equation
[OH-].[Na+].C([O:5][C:6](=[O:44])[C:7]([O:31][C:32]1[CH:33]=[C:34]([C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)[CH:35]=[CH:36][CH:37]=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>[C:34]1([C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)[CH:35]=[CH:36][CH:37]=[C:32]([O:31][C:7]([CH3:30])([CH2:8][C:9]2[CH:10]=[CH:11][C:12]([O:15][CH2:16][CH2:17][C:18]3[N:19]=[C:20]([CH:24]4[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]4)[O:21][C:22]=3[CH3:23])=[CH:13][CH:14]=2)[C:6]([OH:44])=[O:5])[CH:33]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 101667372-(Biphenyl-3-yloxy)-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 223399872-(Biphenyl-3-yloxy)-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-(Biphenyl-3-yloxy)-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 7.51 (d, 2H, J=7.82 Hz), 7.41 (t, 2H, J=7.04 Hz), 7.35-7.24 (m, 2H), 7.18 (d, 3H, J=8.21 Hz), 7.12-7.11 (m, 1H), 6.86 (d, 1H, J=8.60 Hz), 7.82 (d, 2H, J=8.60 Hz), 4.13 (t, 2H, J=5.47 Hz), 3.26 (d, 1H, J=14.08 Hz), 3.14 (d, 1H, J=14.08 Hz), 2.95 (t, 3H, J=5.47 Hz), 2.29 (s, 3H), 2.00 (d, 2H, J=12.51 Hz), 1.79 (d, 2H, J=13.30 Hz), 1.70-1.21 (m, 8H). MS [EI+] 540 (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-23a5da62837f4c9a8d038c94b41be8e2
Source dataset
uspto-grants-2008_03
Patent number
US07345070B2

Reaction notes

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