Water → 3-(3-Benzyloxy-4-fluoro-phenylamino)-but-2-enoic acid ethyl ester

HRID 2415499노트

반응식

HRID 2415499 반응식
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([NH2:16])[CH:12]=[CH:13][C:14]=1[F:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:17]([O:23][CH2:24][CH3:25])(=[O:22])[CH2:18][C:19]([CH3:21])=O.O.C([O-])(O)=O.[Na+]>C1CCCCC1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>[CH2:24]([O:23][C:17](=[O:22])[CH:18]=[C:19]([NH:16][C:11]1[CH:12]=[CH:13][C:14]([F:15])=[C:9]([O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH:10]=1)[CH3:21])[CH3:25]

참가 물질

7

반응물 4

HCID 962WaterHCID 8868Ethyl AcetoacetateHCID 516892Sodium BicarbonateHCID 226414853-Benzyloxy-4-fluoro-phenylamine

생성물 1

HCID 692871753-(3-Benzyloxy-4-fluoro-phenylamino)-but-2-enoic acid ethyl ester수율 100%

시약·촉매·용매 2

HCID 521998p-Toluenesulfonic acid monohydrate촉매HCID 8078Cyclohexane용매

실험 절차

92.7 g (0.43 mol) of 3-Benzyloxy-4-fluoro-phenylamine, 57 ml (0.45 mol) of ethyl acetoacetate and 0.81 g (4 mmol) of p-toluenesulfonic acid monohydrate in 370 ml of cyclohexane were heated at reflux for 3 h in the presence of a water separator funnel. The reaction mixture was cooled to RT, ACOEt (1 l) and saturated aqueous NaHCO3 solution (0.5 l) were added, the layers were separated and the organic layer once extracted with AcOEt (0.3 l). The combined organic layers were dried over magnesium sulfate and concentrated in vacuo to give 140 g (100%) of the desired 3-(3-benzyloxy-4-fluoro-phenylamino)-but-2-enoic acid ethyl ester as yellow-orange crystalline solid. Melting point: 79° C.-80° C.

후처리

  1. customthe layers were separated
  2. extractionthe organic layer once extracted with AcOEt (0.3 l)
  3. dry with materialThe combined organic layers were dried over magnesium sulfate
  4. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-5083ca4956e34c2cac1f041ff4076a48
출처 데이터셋
uspto-grants-2004_11
특허 번호
US06818767B2

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