Methyl iodide → Ethyl 2-[methyl(methylsulfonyl)amino]-1,3-oxazole-4-carboxylate

HRID 14336Notes

Reaction equation

HRID 14336 reaction equation
[CH3:1][S:2]([NH:5][C:6]1[O:7][CH:8]=[C:9]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[N:10]=1)(=[O:4])=[O:3].[C:16](=O)([O-])[O-].[K+].[K+].IC>C(#N)C>[CH3:16][N:5]([S:2]([CH3:1])(=[O:3])=[O:4])[C:6]1[O:7][CH:8]=[C:9]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[N:10]=1

Participants

5

Reactant 3

HCID 6328Methyl iodide2×HCID 11430Potassium CarbonateHCID 21086093Ethyl 2-[(methylsulfonyl)amino]-1,3-oxazole-4-carboxylate

Product 1

HCID 21086092Ethyl 2-[methyl(methylsulfonyl)amino]-1,3-oxazole-4-carboxylate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a 25 ml round bottom flask under N2 was added (101.8mg, 0.4346 mmoles) ethyl 2-[(methylsulfonyl)amino]-1,3-oxazole-4-carboxylate, (180.2 mg, 1.3038 mmoles, 3.0 eq.) potassium carbonate, and (5 ml) acetonitrile. The mixture was then agitated at ambient temperature while (33.8 μl, 0.5429 mmoles, 1.25 eq.) iodomethane was added. The reaction was allowed to run at ambient temperature for 3 hours. An electrospray mass spec indicated mostly starting material. The N2 line was removed and an additional (40 μl, 0.6425 mmoles, 1.5 eq.) iodomethane were added. The reaction was left at ambient temperature overnight. The reaction was quenched with (5 ml) 1N HCl and was extracted with dichloromethane. The organic layer was washed with water and then evaporated to dryness. The resulting oil was purified by preparative HPLC, yielding (70 mg) of ethyl 2-[methyl(methylsulfonyl)amino]-1,3-oxazole-4-carboxylate.

Workup

  1. additionwas added
  2. customThe N2 line was removed
  3. waitThe reaction was left at ambient temperature overnight
  4. customThe reaction was quenched with (5 ml) 1N HCl
  5. extractionwas extracted with dichloromethane
  6. washThe organic layer was washed with water
  7. customevaporated to dryness
  8. customThe resulting oil was purified by preparative HPLC

Sources & evidence

ORD record
ord-6059cfa8f1db4b6f852a89acb59263c1
Source dataset
uspto-grants-2010_06
Patent number
US07727997B2

Reaction notes

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