Hydrochloric Acid → HCID 68491626, compound

HRID 1616541Notes

Reaction equation

HRID 1616541 reaction equation
[OH-].[Na+].C[O:4][C:5](=[O:23])[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12]1[O:13][C:14]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:15][N:16]=1.Cl>O.CO>[C:17]1([C:14]2[O:13][C:12]([CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][C:5]([OH:23])=[O:4])=[N:16][CH:15]=2)[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 59167750Methyl 7-(5-phenyl-1,3-oxazol-2-yl)heptanoate

Product 1

HCID 68491626HCID 68491626, compoundYield 85.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Add a solution of sodium hydroxide (1.80 g, 45.0 mmol) in water (30 mL) to a solution of 7-(5-phenyloxazol-2-yl)heptanoic acid methyl ester (9.0 g, 31.3 mmol) in methanol (30 mL) at room temperature and stir the mixture for 4 hours. Adjust the pH of the mixture to 2 with 1 N HCl and extract with ethyl acetate (500 mL). Wash the combined organic layers with water (3×100 mL), dry over sodium sulfate and remove the solvent under reduced pressure. Crystallize the residue from ethyl acetate/hexanes to afford 7-(5-phenyloxazol-2-yl)heptanoic acid (7.3 g, 85%): APCI mass spectrum m/z 272 [C16H19NO3—H]−.

Workup

  1. extractionextract with ethyl acetate (500 mL)
  2. washWash the combined organic layers with water (3×100 mL)
  3. dry with materialdry over sodium sulfate
  4. customremove the solvent under reduced pressure
  5. customCrystallize the residue from ethyl acetate/hexanes

Sources & evidence

ORD record
ord-7ef27399b6d148ba8c975d62024e626b
Source dataset
uspto-grants-2014_07
Patent number
US08765796B2

Reaction notes

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