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

HRID 1474008

반응식

HRID 1474008 반응식
[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]

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

반응 조건

온도
60 °C

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-5190e91344024ebea7a6c9abb9757fb5
출처 데이터셋
uspto-grants-2015_04
특허 번호
US09018209B2

연결된 노트

불러오는 중…