Hydrochloric Acid → 3-(Ethoxycarbonyl)-5-methyl-1,2-oxazole-4-carboxylic acid

HRID 1685044Notes

Reaction equation

HRID 1685044 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:10]([C:11]([O:13]C(C)(C)C)=[O:12])=[C:9]([CH3:18])[O:8][N:7]=1)=[O:5])[CH3:2].Cl>C(O)=O>[CH2:1]([O:3][C:4]([C:6]1[C:10]([C:11]([OH:13])=[O:12])=[C:9]([CH3:18])[O:8][N:7]=1)=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 57571514HCID 57571514, compound

Product 1

HCID 178320283-(Ethoxycarbonyl)-5-methyl-1,2-oxazole-4-carboxylic acid

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

The tert-butyl ester obtained in Step 2 (0.8 g, 3.13 mmol) was dissolved in formic acid (20 mL) and stirred at room temperature overnight. 6N aq. HCl (50 ml) was added. The mixture was extracted with DCM (3×50 mL). The combined organic layers were dried over sodium sulfate and concentrated to give the title compound, Intermediate 35: 3-(ethoxycarbonyl)-5-methylisoxazole-4-carboxylic acid, as a brownish oil (0.4 g, 64%). 1H NMR (300 MHz, MeOH-d4): δ 4.40 (q, 2H), 2.68 (s, 3H), 1.35 (t, 3H).

Workup

  1. extractionThe mixture was extracted with DCM (3×50 mL)
  2. dry with materialThe combined organic layers were dried over sodium sulfate
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-52f9bec378b44a94886a0eb202c8f76c
Source dataset
uspto-grants-2012_04
Patent number
US08148380B2

Reaction notes

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