Hydrochloric Acid → HCID 10994825, compound

HRID 398200Notes

Reaction equation

HRID 398200 reaction equation
C[O:2][C:3](=[O:38])[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:26]3[CH:31]=[CH:30][C:29]([C:32]4[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=4)=[CH:28][CH:27]=3)[O:20][C:21]=2[C:22]([F:25])([F:24])[F:23])=[CH:10][CH:9]=1)([CH3:6])[CH3:5].[OH-].[Na+].Cl>C(O)C>[C:29]1([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[CH:28]=[CH:27][C:26]([C:19]2[O:20][C:21]([C:22]([F:25])([F:24])[F:23])=[C:17]([CH2:16][CH2:15][O:14][C:11]3[CH:12]=[CH:13][C:8]([O:7][C:4]([CH3:6])([CH3:5])[C:3]([OH:38])=[O:2])=[CH:9][CH:10]=3)[N:18]=2)=[CH:31][CH:30]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 11092613HCID 11092613, compound

Product 1

HCID 10994825HCID 10994825, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

A sample of 2-{4-[2-(2-biphenyl-4-yl-5-trifluoromethyloxazol-4-yl)-ethoxy]-phenoxy}-2-methyl-propionic acid methyl ester (141 mg, 0.21 mmol) was dissolved in ethanol (2 mL) followed by addition of 5.0 N NaOH (0.6 mL). The mixture was warmed with magnetic stirring at 50° C. for one hour. The reaction mixture was then allowed to cool to room temperature then acidified with 1.0 N HCl (3 mL) then extracted with methylene chloride (50 mL). The organic phase was separated, dried over sodium chloride and concentrated under reduced pressure to yield 134 mg (98%, 24% overall) of a glassy solid. HPLC RT1=5.90 min; 1H NMR (400 MHz, CDCl3) δ8.08 (d, J=8.3 Hz, 2H), 7.67 (d, J=8.3 Hz, 2H), 7.60 (d, J=8.3 Hz, 2H), 7.45-7.36 (m, 3H), 6.86 (d, J=9.3 Hz, 2H), 6.78 (d, J=9.3 Hz, 2H), 4.24 (t, J=6.3 Hz, 2H), 3.15 (t, J=6.3 Hz, 2H), 1.48 (s, 6H); MS (EI) 511.95 (M+H)+.

Workup

  1. temperatureThe mixture was warmed
  2. temperatureto cool to room temperature
  3. extractionthen extracted with methylene chloride (50 mL)
  4. customThe organic phase was separated
  5. dry with materialdried over sodium chloride
  6. concentrationconcentrated under reduced pressure
  7. customto yield 134 mg (98%, 24% overall) of a glassy solid
  8. customHPLC RT1=5.90 min

Sources & evidence

ORD record
ord-5385a11113624601984d640de8d55f9f
Source dataset
uspto-grants-2003_08
Patent number
US06610696B2

Reaction notes

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