Ethyl bromopyruvate → Ethyl 2-(3-hydroxy-4-methylphenylamino)oxazole-4-carboxylate

HRID 1474008

反応式

HRID 1474008 の反応式
[OH:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]([NH2:12])=[O:11])[CH:5]=[CH:6][C:7]=1[CH3:8].Br[CH2:14][C:15](=O)[C:16]([O:18][CH2:19][CH3:20])=[O:17]>CN(C=O)C.CCOC(C)=O>[OH:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]2[O:11][CH:14]=[C:15]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[N:12]=2)[CH:5]=[CH:6][C:7]=1[CH3:8]

参加物

5

反応物 2

HCID 66144Ethyl bromopyruvateHCID 85554(3-Hydroxy-p-tolyl)urea

生成物 1

HCID 68491443Ethyl 2-(3-hydroxy-4-methylphenylamino)oxazole-4-carboxylate収率 50%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
60 °C

実験手順

A solution containing 1-(3-hydroxy-4-methylphenyl)urea (150 mg, 0.9 mmol) and ethyl 3-bromopyruvate (0.11 mL, 0.9 mmol) in dry DMF (3.611E) was heated at 60° C. for 6 h. The reaction mixture was diluted with EtOAc and washed with brine and saturated NaHCO3 solution and the combined organic layers were dried (Na2SO4) and concentrated. The crude product was purified by flash chromatography on silica gel (hexane:EtOAc 6/4) to give the product in 50% yield (119 mg).

後処理

  1. washwashed with brine and saturated NaHCO3 solution
  2. dry with materialthe combined organic layers were dried (Na2SO4)
  3. concentrationconcentrated
  4. customThe crude product was purified by flash chromatography on silica gel (hexane:EtOAc 6/4)
  5. customto give the product in 50% yield (119 mg)

出典と根拠

ORDレコード
ord-5190e91344024ebea7a6c9abb9757fb5
出典データセット
uspto-grants-2015_04
特許番号
US09018209B2

関連ノート

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