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Hydrochloric Acid → HCID 67258482, 화합물

HRID 1467691
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HRID 1467691 반응식
[O:1]=[C:2]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:3]([NH:5][C:6]1[CH:14]=[CH:13][CH:12]=[C:11]2[C:7]=1[CH2:8][O:9][C:10]2=[O:15])=[O:4].[H-].[Na+].Cl[CH2:25][C:26]1[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[CH:28][CH:27]=1.Cl>CN(C=O)C.C(OCC)(=O)C.O>[CH3:33][O:32][C:29]1[CH:30]=[CH:31][C:26]([CH2:25][N:5]([C:6]2[CH:14]=[CH:13][CH:12]=[C:11]3[C:7]=2[CH2:8][O:9][C:10]3=[O:15])[C:3](=[O:4])[C:2](=[O:1])[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[CH:27][CH:28]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

8

반응물 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 699934-Methyloxybenzyl chlorideHCID 67386784HCID 67386784, 화합물

생성물 1

HCID 67258482HCID 67258482, 화합물수율 66%

시약·촉매·용매 3

HCID 962Water용매
HCID 6228
Dimethylformamide
용매
HCID 8857Ethyl Acetate용매

실험 절차

To a solution of 2-oxo-N-(1-oxo-1,3-dihydroisobenzofuran-4-yl)-2-phenylacetamide (5 g, 11.7 mmol) in DMF (48 mL) was added NaH (0.78 g, 19.5 mmol). The solution was stirring at room temperature for 1.5 hr, followed by the addition of 1-(chloromethyl)-4-methoxy-benzene (2.8 mL). After stirred at 30° C. overnight, the resulting mixture was added water and adjusted to pH=3-4 with 0.5 N aq. HCl. Then ethyl acetate was added, concentrated and filtered, the filtrate was washed by ethyl acetate, the combine ethyl acetate layer was washed with brine, dried over anhydrous sodium sulfate, concentrated, and purified by flash chromatography on silica gel to obtain the desired compound (4.7 g, yield 66%). LC-MS (ESI) m/z: 402 (M+1)+. 1H-NMR (400 MHz, DMSO-d) δ (ppm): 3.73 (s, 3H), 4.83-5.17 (m, 4H), 6.89-6.91 (d, J=8.8 Hz, 2H), 7.18-7.20 (m, 2H), 7.24-7.26 (m, 1H), 7.38-7.42 (t, 1H), 7.52-7.56 (m, 2H), 7.69-7.71 (m, 1H), 7.75-7.81 (m, 3H).

후처리

  1. stirringAfter stirred at 30° C. overnight
  2. concentrationconcentrated
  3. filtrationfiltered
  4. washthe filtrate was washed by ethyl acetate
  5. washthe combine ethyl acetate layer was washed with brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated
  8. custompurified by flash chromatography on silica gel

출처 및 근거

ORD 기록
ord-2b7d849256b5443da7bb92519ee0ffb0
출처 데이터셋
uspto-grants-2015_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08999987B2

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