Carbon Dioxide → 4-Cyclopropylaminocarbonyl-2-isopropyloxazole-5-carboxylic acid

HRID 1656897

反応式

HRID 1656897 の反応式
C([Li])CCC.[CH:6]1([NH:9][C:10]([C:12]2[N:13]=[C:14]([CH:17]([CH3:19])[CH3:18])[O:15][CH:16]=2)=[O:11])[CH2:8][CH2:7]1.[C:20](=[O:22])=[O:21]>CCCCCC.O1CCCC1>[CH:6]1([NH:9][C:10]([C:12]2[N:13]=[C:14]([CH:17]([CH3:19])[CH3:18])[O:15][C:16]=2[C:20]([OH:22])=[O:21])=[O:11])[CH2:7][CH2:8]1

参加物

6

反応物 3

HCID 280Carbon DioxideHCID 156724292-Isopropyl-oxazole-4-carboxylic acid-cyclopropylamideHCID 178418339Butyllithium

生成物 1

HCID 156724304-Cyclopropylaminocarbonyl-2-isopropyloxazole-5-carboxylic acid収率 81%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8058Hexane溶媒

実験手順

At -70° C. and under a nitrogen blanket, 0.12 mol of n-butyllithium (80.0 ml of a 1.5 molar solution in hexane) was dripped into a solution of 10.4 g (0.054 mol) of 2-isopropyloxazole-4-carboxylic acid-cyclopropylamide in 250 ml of tetrahydrofuran, and the mixture was stirred for 30 minutes at this temperature. The reaction mixture was then poured onto 500 g of solid CO2 and allowed to stand overnight. The residue remaining after evaporating down was taken up in 200 ml of water and 30 ml of 2N NaOH, the solution was extracted twice, each time with 100 ml of diethyl ether, the aqueous phase was acidified to a pH of 2 with concentrated hydrochloric acid and the solution extracted three times, each time with 200 ml of ethyl acetate. Drying over magnesium sulfate and removal of the solvent under reduced pressure gave 10.4 g (81%) of 4-cyclopropylaminocarbonyl-2-isopropyloxazole-5-carboxylic acid as a white powder of m.p. 109°-112° C. (active ingredient no. 3.007).

後処理

  1. customAt -70° C.
  2. waitto stand overnight
  3. customafter evaporating down
  4. extraction30 ml of 2N NaOH, the solution was extracted twice
  5. extractionthe solution extracted three times
  6. dry with materialDrying over magnesium sulfate and removal of the solvent under reduced pressure

出典と根拠

ORDレコード
ord-cb1f52e7da164dada609c04ae0e84343
出典データセット
uspto-grants-1993_10
特許番号
US05256633

関連ノート

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