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

HRID 349125ノート

反応式

HRID 349125 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

To a 25 ml round bottom flask under N2 was added (101.8 mg, 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.

後処理

  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

出典と根拠

ORDレコード
ord-ddf867c60a6747c59d5e503d197d1068
出典データセット
uspto-grants-2007_02
特許番号
US07176242B2

反応ノート

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