Benzyl acetoacetate → (E)-3-[4-(tert-Butoxycarbonylamino-methyl)-2-iodo-phenylamino]-but-2-enoic Acid Benzyl Ester

HRID 966533노트

반응식

HRID 966533 반응식
[C:1]([O:5][C:6](=[O:17])[NH:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([NH2:15])=[C:11]([I:16])[CH:10]=1)([CH3:4])([CH3:3])[CH3:2].[C:18]([O:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)(=[O:23])[CH2:19][C:20]([CH3:22])=O>C1C=CC=CC=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>[CH2:25]([O:24][C:18](=[O:23])/[CH:19]=[C:20](/[NH:15][C:12]1[CH:13]=[CH:14][C:9]([CH2:8][NH:7][C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:17])=[CH:10][C:11]=1[I:16])\[CH3:22])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

참가 물질

5

반응물 2

HCID 142266Benzyl acetoacetateHCID 10383091tert-Butyl 4-amino-3-iodobenzylcarbamate

생성물 1

HCID 23393855(E)-3-[4-(tert-Butoxycarbonylamino-methyl)-2-iodo-phenylamino]-but-2-enoic Acid Benzyl Ester수율 100.5%

시약·촉매·용매 2

HCID 6101p-Toluenesulfonic acid촉매HCID 241Benzene용매

실험 절차

To a solution of (4-amino-3-iodo-benzyl)-carbamic acid tert-butyl ester (3.5 g, 10 mmol) and benzyl acetoacetate (1.92 g, 10 mmol) in benzene (80 mL) was added p-toluenesulfonic acid (95 mg, 0.5 mmol). The mixture was heated at reflux overnight using a Dean Stark condenser. The mixture was washed with water and brine, dried over Na2SO4 and filtered. The filtrate was concentrated in vacuo to give 5.25 g (99%) of crude desired product as a light brown oil: MS(APCI+): m/z 523.1 (MH+). The compound was taken to Step D without further purification.

후처리

  1. temperatureThe mixture was heated
  2. temperatureat reflux overnight
  3. washThe mixture was washed with water and brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated in vacuo

출처 및 근거

ORD 기록
ord-f71db7501cf645a0817b30333b094c68
출처 데이터셋
uspto-grants-2005_10
특허 번호
US06951848B2

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