Sodium hydride → Diethyl 2-(tert-butoxyformamido)-2-[(5-oxazolyl)methyl]malonate

HRID 635641

反応式

HRID 635641 の反応式
[H-].[Na+].[C:3]([O:7][C:8]([NH:10][CH:11]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[C:12]([O:14][CH2:15][CH3:16])=[O:13])=[O:9])([CH3:6])([CH3:5])[CH3:4].Cl[CH2:23][C:24]1[O:28][CH:27]=[N:26][CH:25]=1>C(O)C>[C:3]([O:7][C:8]([NH:10][C:11]([CH2:23][C:24]1[O:28][CH:27]=[N:26][CH:25]=1)([C:12]([O:14][CH2:15][CH3:16])=[O:13])[C:17]([O:19][CH2:20][CH3:21])=[O:18])=[O:9])([CH3:6])([CH3:4])[CH3:5]

参加物

5

反応物 3

HCID 24758Sodium hydrideHCID 382219Diethyl 2-((tert-butoxycarbonyl)amino)malonateHCID 152908805-(Chloromethyl)-1,3-oxazole

生成物 1

HCID 70092767Diethyl 2-(tert-butoxyformamido)-2-[(5-oxazolyl)methyl]malonate

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

反応条件

温度
0 °C

実験手順

301 mg of a 60% dispersion of sodium hydride in mineral oil were added portionwise to 60 ml of anhydrous ethanol at 0° C. and the resulting suspension was stirred at 0° C. for 5 minutes. 1.88 g of diethyl 2-(tert-butoxyformamido)malonate were added and the mixture was warmed to room temperature. After stirring at room temperature for 10 minutes 805 mg of 5-(chloromethyl)oxazole were added. The mixture was stirred at room temperature for 30 minutes and at 60° C. for 1 hour. The solvent was evaporated and the crude product was dissolved in diethyl ether and washed with water. Sodium chloride was added to the aqueous layer, which was then extracted with diethyl ether. The combined organic layers were dried over magnesium sulphate and the solvent was removed by evaporation. Purification of the residue by chromatography on silica gel using ethyl acetate/hexane (1:2) for the elution gave diethyl 2-(tert-butoxyformamido)-2-[(5-oxazolyl)methyl]malonate, 1H NMR (250 MHz, CDCl3) δ: 1.3 (t,6H), 1.45 (s,9H), 3.75 (s,2H), 4.2 (m,4H), 5.85 (s,1H), 6.8 (s,1H), 7.75 (s,1H).

後処理

  1. temperaturethe mixture was warmed to room temperature
  2. additionwere added
  3. stirringThe mixture was stirred at room temperature for 30 minutes and at 60° C. for 1 hour
  4. customThe solvent was evaporated
  5. dissolutionthe crude product was dissolved in diethyl ether
  6. washwashed with water
  7. additionSodium chloride was added to the aqueous layer, which
  8. extractionwas then extracted with diethyl ether
  9. dry with materialThe combined organic layers were dried over magnesium sulphate
  10. customthe solvent was removed by evaporation
  11. customPurification of the residue by chromatography on silica gel
  12. washfor the elution

出典と根拠

ORDレコード
ord-f05699401b8847e68994ecec9e2d6bc7
出典データセット
uspto-grants-2001_02
特許番号
US06187905B1

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