Hydrochloric Acid → (2-Cyclohexyl-5-methyl-oxazol-4-yl)-acetic acid

HRID 2215206Notes

Reaction equation

HRID 2215206 reaction equation
[CH:1]1([C:7]2O[C:9]([CH3:15])=[C:10](CC#N)[N:11]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[OH-:16].[Na+].Cl.CC[O:21][C:22]([CH3:24])=[O:23]>CCO.O>[CH:1]1([C:7]2[O:16][C:9]([CH3:15])=[C:10]([CH2:24][C:22]([OH:21])=[O:23])[N:11]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 15343904(2-Cyclohexyl-5-methyl-oxazol-4-yl)-acetonitrile

Product 1

HCID 10857080(2-Cyclohexyl-5-methyl-oxazol-4-yl)-acetic acid

Reagents, catalysts & solvents 1

HCID 19096565Water ethanolSolvent

Procedure

1.900 g of the above prepared (2-cyclohexyl-5-methyl-oxazol-4-yl)-acetonitrile (9.30 mmol) was dissolved in 21 ml EtOH/water=1/1 and treated with 5 eq. of NaOH-pellets (1.86 g). Hydrolysis was allowed to proceed over night at 60° C. After cooling, 25% HCl was added, followed by AcOEt. After separation of the two layers, the aq. phase was again extracted with AcOEt, the combined organic layers washed with water, dried over sodium sulfate, and evaporated to dryness to yield 1.920 g of the title acid as light-brown, waxy solid.

Workup

  1. customHydrolysis
  2. waitto proceed over night at 60° C
  3. temperatureAfter cooling
  4. customAfter separation of the two layers
  5. extractionthe aq. phase was again extracted with AcOEt
  6. washthe combined organic layers washed with water
  7. dry with materialdried over sodium sulfate
  8. customevaporated to dryness
  9. customto yield 1.920 g of the title acid as light-brown, waxy solid

Sources & evidence

ORD record
ord-e2db40434a7e4513900f2ab5d9b25702
Source dataset
uspto-grants-2006_09
Patent number
US07109225B2

Reaction notes

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