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Water → Ethyl 3-(benzyloxy)-4-oxo-6,7,8,9-tetrahydro-4H-7,10-ethanopyrimido[1,2-a][1,3]diazepine-2-carboxylate

HRID 1093119
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HRID 1093119 반응식
[CH2:1]([O:8][C:9]1[C:14](=[O:15])[N:13](S(C)(=O)=O)[C:12]([N:20]2[CH2:25][CH2:24][CH:23]([CH2:26]OS(C)(=O)=O)[CH2:22][CH2:21]2)=[N:11][C:10]=1[C:32]([O:34][CH2:35][CH3:36])=[O:33])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].O>C(O)C>[CH2:1]([O:8][C:9]1[C:14](=[O:15])[N:13]2[CH2:26][CH:23]3[CH2:24][CH2:25][N:20]([C:12]2=[N:11][C:10]=1[C:32]([O:34][CH2:35][CH3:36])=[O:33])[CH2:21][CH2:22]3)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1
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참가 물질

5

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HCID 962WaterHCID 11430Potassium CarbonateHCID 57904840Ethyl 5-(benzyloxy)-1-(methylsulfonyl)-2-(4-((methylsulfonyloxy)methyl)piperidin-1-yl)-6-oxo-1,6-dihydropyrimidine-4-carboxylate

생성물 1

HCID 57904901Ethyl 3-(benzyloxy)-4-oxo-6,7,8,9-tetrahydro-4H-7,10-ethanopyrimido[1,2-a][1,3]diazepine-2-carboxylate수율 37%

시약·촉매·용매 1

HCID 702
Ethanol
용매

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온도
60 °C

실험 절차

A mixture of ethyl 5-(benzyloxy)-1-(methylsulfonyl)-2-(4-((methylsulfonyloxy)methyl)piperidin-1-yl)-6-oxo-1,6-dihydropyrimidine-4-carboxylate and K2CO3 (0.051 g, 0.368 mmol) in ethanol (10 mL) was stirred at 60° C. for 4 h and cooled to room temperature. Water was added and the product was extracted with ethyl acetate. The organic phase was washed with brine then dried (Na2SO4), filtered and concentrated. The residue was purified by flash column chromatography (Biotage flash chromatography system; 0%-10% methanol/CH2Cl2, 25 CV; 10% methanol/CH2Cl2, 5 CV) to give the title compound as a white glass (0.0248 g, 37% yield). 1H NMR (500 MHz, CDCl3) δ: 7.44 (2H, dd, J=7.3 Hz), 7.30-7.22 (3H, m), 5.27 (2H, s), 4.22 (2H, q, J=7.1 Hz), 4.01-3.94 (2H, m), 3.77-3.70 (2H, m), 3.67 (2H, brs), 3.02 (1H, brs), 2.29-2.24 (2H, m), 1.93-1.88 (2H, m), 1.22 (3H, t, J=7.0 Hz). LCMS (M+H) calcd for C20H24N3O4: 370.17; found: 370.30.

후처리

  1. temperaturecooled to room temperature
  2. extractionthe product was extracted with ethyl acetate
  3. washThe organic phase was washed with brine
  4. dry with materialthen dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by flash column chromatography (Biotage flash chromatography system; 0%-10% methanol/CH2Cl2, 25 CV; 10% methanol/CH2Cl2, 5 CV)

출처 및 근거

ORD 기록
ord-70d3af1f637249cd96fa588b809a33e0
출처 데이터셋
uspto-grants-2012_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08129398B2

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