(3-Ethyl-5-methylisoxazol-4-yl)-carbamic acid 2-trimethylsilanylethyl ester → HCID 22456668, compound

HRID 2186455Notes

Reaction equation

HRID 2186455 reaction equation
C[Si](C)(C)CCOC(=O)[NH:7][C:8]1[C:9]([CH2:14][CH3:15])=[N:10][O:11][C:12]=1[CH3:13]>[F-].C([N+](CCCC)(CCCC)CCCC)CCC.O1CCCC1>[CH2:14]([C:9]1[C:8]([NH2:7])=[C:12]([CH3:13])[O:11][N:10]=1)[CH3:15]

Participants

4

Reactant 1

HCID 69838742(3-Ethyl-5-methylisoxazol-4-yl)-carbamic acid 2-trimethylsilanylethyl ester

Product 1

HCID 22456668HCID 22456668, compoundYield 41.7%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 2724141Tetrabutylammonium FluorideSolvent

Procedure

A solution of (3-ethyl-5-methylisoxazol-4-yl)-carbamic acid 2-trimethylsilanylethyl ester (1.8 g) in tetrabutylammonium fluoride (26.7 ml of a 1.0M solution in tetrahydrofuran) was heated at 50° C. for 30 mins. The solvent was removed in vacuo and the residue dissolved in ethyl acetate (150 ml), washed with sodium hydrogencarbonate solution (30 ml), washed with water (30 ml) and washed with brine (30 ml). The organic layer was separated, dried over magnesium sulphate, filtered and the solvent removed in vacuo. Purification by column chromatography on silica eluting with 50-100% ethyl acetate in hexane afforded the title compound as a yellow oil (0.35 g).

Workup

  1. customThe solvent was removed in vacuo
  2. dissolutionthe residue dissolved in ethyl acetate (150 ml)
  3. washwashed with sodium hydrogencarbonate solution (30 ml)
  4. washwashed with water (30 ml)
  5. washwashed with brine (30 ml)
  6. customThe organic layer was separated
  7. dry with materialdried over magnesium sulphate
  8. filtrationfiltered
  9. customthe solvent removed in vacuo
  10. customPurification by column chromatography on silica eluting with 50-100% ethyl acetate in hexane

Sources & evidence

ORD record
ord-450b773583c84748a6269b83136bb9e3
Source dataset
uspto-grants-2002_06
Patent number
US06403791B1

Reaction notes

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