Hydrochloric Acid → HCID 178472438, 화합물

HRID 1631435노트

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HRID 1631435 반응식
[NH2:1][C@H:2]1[CH2:7][CH2:6][C@H:5]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH2:4][CH2:3]1.Cl.C([O-])([O-])=O.[K+].[K+].Br[CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>C(#N)C>[CH2:21]([N:1]([CH2:8][C:5]1[CH:6]=[CH:7][CH:2]=[CH:3][CH:4]=1)[C@H:2]1[CH2:3][CH2:4][C@H:5]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH2:6][CH2:7]1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 178472434HCID 178472434, 화합물

생성물 1

HCID 178472438HCID 178472438, 화합물수율 91%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

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온도
80 °C

실험 절차

A stirred suspension of 13A.HCl (5.12 g, 24.65 mmol) in acetonitrile (75 mL) was treated with K2CO3 (13.63 g, 99 mmol) and (bromomethyl)benzene (7.32 mL, 61.6 mmol). The resulting suspension was stirred at 80° C. overnight. Upon cooling, the solid was filtered off and filtrate was concentrated. The residue was purified by Isco silica column (80 g) eluted with ethyl acetate-hexane: 0%-20%. Concentration of the appropriate fractions provided 13B (7.92 g, 91% yield) as a colorless oil. MS (ES): m/z=352.2 [M+H]+. 1H NMR (400 MHz, CDCl3) δ ppm 7.08-7.34 (m, 10H); 4.01 (q, 2H, J=7.1 Hz); 3.55 (s, 4H); 2.40-2.49 (m, 1H); 2.06-2.14 (m, 1H); 1.86-2.00 (m, 2H); 1.24-1.38 (m, 2H); 1.18 (t, 3H, J=7.1 Hz).

후처리

  1. temperatureUpon cooling
  2. filtrationthe solid was filtered off
  3. concentrationfiltrate was concentrated
  4. customThe residue was purified by Isco silica column (80 g)
  5. washeluted with ethyl acetate-hexane

출처 및 근거

ORD 기록
ord-28fba15365064698af6abff01dc18eab
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08791257B2

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