Sodium Hydroxide → HCID 11812904, compound

HRID 2417119Notes

Reaction equation

HRID 2417119 reaction equation
C[O:2][C:3](=[O:37])[C:4]([O:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][CH2:15][CH2:16][C:17]2[N:18]=[C:19]([C:25]3[CH:30]=[CH:29][C:28]([C:31]4[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=4)=[CH:27][CH:26]=3)[O:20][C:21]=2[CH2:22][CH2:23][CH3:24])=[CH:10][CH:9]=1)([CH3:6])[CH3:5].[OH-].[Na+]>C(O)C>[C:28]1([C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=2)[CH:27]=[CH:26][C:25]([C:19]2[O:20][C:21]([CH2:22][CH2:23][CH3:24])=[C:17]([CH2:16][CH2:15][O:14][C:11]3[CH:12]=[CH:13][C:8]([O:7][C:4]([CH3:5])([CH3:6])[C:3]([OH:37])=[O:2])=[CH:9][CH:10]=3)[N:18]=2)=[CH:30][CH:29]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 10907217HCID 10907217, compound

Product 1

HCID 11812904HCID 11812904, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

A sample of 2-{4-[2-(2-biphenyl-4-yl-5-propyl-oxazol-4-yl)-ethoxy]-phenoxy}-2-methyl-propionic acid methyl ester (484 mg, 0.97 mmol) was dissolved in ethanol (5 mL) followed by addition of 5.0 N NaOH (2 mL). The mixture was warmed with magnetic stirring at 50° C. for two hours. The reaction mixture was then allowed to cool to room temperature then partitioned between 50 mL of methylene chloride and 15 mL of 1.0 N HCl. The organic phase was separated, dried over sodium chloride and concentrated in vacuo to yield 384 mg (82%)of a glassy solid. HPLC RT1=6.37 min; 1H NMR (400 MHz, CDCl3) δ 8.01 (d, J=8.3 Hz, 2H), 7.63-7.58 (m, 4H), 7.43-7.33 (m, 3H), 6.86 (d, J=9.3 Hz, 2H), 6.73 (d, J=9.3 Hz, 2H), 4.13 (t, J=6.3 Hz, 2H), 2.97 (t, J=6.3 Hz, 2H), 2.66 (t, J=7.3 Hz, 2H), 1.73-1.68 (m, 2H), 1.49 (s, 6H), 0.98 (t, J=7.3 Hz, 3H); MS (EI) 486.33 (M+H)+, 484.37 (M−H)−.

Workup

  1. temperatureThe mixture was warmed
  2. temperatureto cool to room temperature
  3. customthen partitioned between 50 mL of methylene chloride and 15 mL of 1.0 N HCl
  4. customThe organic phase was separated
  5. dry with materialdried over sodium chloride
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1c14ccc9937d4ebd9745f40e8eb80c0a
Source dataset
uspto-grants-2004_11
Patent number
US06825222B2

Reaction notes

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