Ethyl Acetate → HCID 66894693, 화합물

HRID 19393노트

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HRID 19393 반응식
Cl.[CH3:2][O:3][C:4](=[O:11])[C@H:5]([CH2:7][CH:8]([CH3:10])[CH3:9])[NH2:6].C([O:14][C:15](=O)/[CH:16]=[C:17](/[O:20][C:21]1[C:26]2[N:27]=[C:28]([CH3:30])[O:29][C:25]=2[CH:24]=[CH:23][CH:22]=1)\[CH2:18]Br)C.C(N(CC)C(C)C)(C)C.C(OCC)(=O)C>C(#N)C>[CH3:2][O:3][C:4](=[O:11])[C@@H:5]([N:6]1[CH2:18][C:17]([O:20][C:21]2[C:26]3[N:27]=[C:28]([CH3:30])[O:29][C:25]=3[CH:24]=[CH:23][CH:22]=2)=[CH:16][C:15]1=[O:14])[CH2:7][CH:8]([CH3:10])[CH3:9]

참가 물질

6

반응물 4

HCID 8857Ethyl AcetateHCID 81531DiisopropylethylamineHCID 2723695Leucine methyl ester hydrochlorideHCID 66894865(E)-4-bromo-3-(2-methyl-benzooxazol-4-yloxy)-but-2-enoic acid ethyl ester

생성물 1

HCID 66894693HCID 66894693, 화합물수율 56%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

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온도
100 °C

실험 절차

A mixture of (L)-leucine methyl ester hydrochloride (0.570 g, 3.14 mmol), (E)-4-bromo-3-(2-methyl-benzooxazol-4-yloxy)-but-2-enoic acid ethyl ester (0.970 g, 2.85 mmol) and N,N-diisopropylethylamine (0.809 g, 6.21 mmol) in acetonitrile (20 mL) in a sealed tube was heated at 100° C. for 5 h. The reaction mixture was then cooled to room temperature and ethyl acetate was added. The mixture was then filtered. The filtrate was washed successively with aqueous saturated ammonium chloride, water, and brine and then dried over sodium sulfate, filtered and concentrated in vacuo. The residue was dissolved in tetrahydrofuran (5 mL) and microwaved in an Emry Optimizer microwave reaction vessel at 160° C., for 3 h. The mixture was then cooled and concentrated in vacuo and the residue was purified by ISCO Combiflash chromatography (40 g Silicycle, 5% to 50% ethyl acetate/hexanes) to afford (S)-4-methyl-2-[4-(2-methyl-benzooxazol-4-yloxy)-2-oxo-2,5-dihydro-pyrrol-1-yl]-pentanoic acid methyl ester (0.570 g, 56%) as a brown oil.

후처리

  1. temperatureThe reaction mixture was then cooled to room temperature
  2. filtrationThe mixture was then filtered
  3. washThe filtrate was washed successively with aqueous saturated ammonium chloride, water, and brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. dissolutionThe residue was dissolved in tetrahydrofuran (5 mL)
  8. custommicrowaved in an Emry Optimizer microwave reaction vessel at 160° C., for 3 h
  9. temperatureThe mixture was then cooled
  10. concentrationconcentrated in vacuo
  11. customthe residue was purified by ISCO Combiflash chromatography (40 g Silicycle, 5% to 50% ethyl acetate/hexanes)

출처 및 근거

ORD 기록
ord-c340630b5e7a4d41953dd76d267699a5
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07741327B2

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