Hydrochloric Acid → HCID 57571514, compound

HRID 1685043Notes

Reaction equation

HRID 1685043 reaction equation
[CH2:1]([O:3][C:4](=[O:18])[C:5](=O)[CH:6]([C:14](=[O:16])[CH3:15])[C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH3:2].C([N:21](CC)CC)C.Cl.NO.Cl>C(Cl)(Cl)Cl>[CH2:1]([O:3][C:4]([C:5]1[C:6]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])=[C:14]([CH3:15])[O:16][N:21]=1)=[O:18])[CH3:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 443297Hydroxyamine hydrochlorideHCID 86661302HCID 86661302, compound

Product 1

HCID 57571514HCID 57571514, compoundYield 77.8%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

The 1,3-diketone obtained in Step 1 (34.7 mmol, 8.9 g) was dissolved in chloroform (50 ml). 4.91 g of triethylamine (1.4 eq, 48.6 mmol) and hydroxylamine-HCl salt (1.3 eq, 45.1 mmol, 3.13 g) were added and the mixture was refluxed for 3 h. The reaction was cooled to room temperature and 1N aq. HCl (100 ml) was added followed by extraction with DCM (3×100 mL). The combined organic layers were dried over sodium sulfate, filtered and concentrated. Column purification by silica gel yielded (6.89 g, 77% yield) of tert-butyl 3-(ethoxycarbonyl)-5-methylisoxazole-4-carboxylate. 1H NMR (300 MHz, CDCl3), δ 4.42 (q, 2H), 2.66 (s, 3H), 1.53 (s, 15H), 1.39 (t, 3H).

Workup

  1. temperaturethe mixture was refluxed for 3 h
  2. extractionfollowed by extraction with DCM (3×100 mL)
  3. dry with materialThe combined organic layers were dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customColumn purification by silica gel

Sources & evidence

ORD record
ord-e1c4650d158940c7b4fd9ab6913f4df5
Source dataset
uspto-grants-2012_04
Patent number
US08148380B2

Reaction notes

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