Ethyl Acetate → 4-{[(Benzyloxy)amino]carbonyl}phenyl 1-(4-methoxyphenyl)cyclohexanecarboxylate

HRID 2375236노트

반응식

HRID 2375236 반응식
[CH2:1]([O:8][NH:9][C:10](=[O:18])[C:11]1[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:19][O:20][C:21]1[CH:26]=[CH:25][C:24]([C:27]2([C:33](Cl)=[O:34])[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]2)=[CH:23][CH:22]=1.C(OCC)(=O)C>CN(C)C1C=CN=CC=1.O1CCCC1>[CH3:19][O:20][C:21]1[CH:26]=[CH:25][C:24]([C:27]2([C:33]([O:17][C:14]3[CH:13]=[CH:12][C:11]([C:10]([NH:9][O:8][CH2:1][C:2]4[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=4)=[O:18])=[CH:16][CH:15]=3)=[O:34])[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]2)=[CH:23][CH:22]=1

참가 물질

6

반응물 3

HCID 8857Ethyl AcetateHCID 27596461-(4-Methoxyphenyl)cyclohexanecarbonyl chlorideHCID 58611844N-(Benzyloxy)-4-hydroxybenzamide

생성물 1

HCID 586118514-{[(Benzyloxy)amino]carbonyl}phenyl 1-(4-methoxyphenyl)cyclohexanecarboxylate수율 52%

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 8028Tetrahydrofuran용매2회

실험 절차

To a solution of N-(benzyloxy)4-hydroxybenzamide (14) (0.078 g, 0.32 mmol) and 4-dimethylaminopyridine (0.047 g, 0.38 mmol) in tetrahydrofuran (2 ml) under argon atmosphere at ice bath temperature a solution of 1-(4-methoxyphenyl) cyclohexanecarbonyl chloride (21a) (0.082 g, obtained in the preceding step of the synthesis) in tetrahydrofuran (2 ml) was added. The resultant white suspension was stirred at room temperature overnight and poured into ethyl acetate (80 ml). The ethyl acetate extract was washed with water (50 ml), brine (30 ml), and dried (Na2SO4). The solvent was evaporated and the residue was dissolved in a small amount of benzene (0.5-1 ml). The precipitated solid was filtered off, the filtrate was evaporated and chromatographed on silicagel (10 g) with benzene-ethyl acetate (9:1) as eluent affording the title compound (0.077 g, 52% based on 1/1) as a white solid. 1H NMR (DMSO-d6, HMDSO) δ: 1.07-2.01 (8H, m); 2.21-2.61 (2H, m, overlapped with a signal of DMSO); 3.75 (3H, s); 4.92 (2H, s); 6.97 (2H, d, J=8.5 Hz); 7.04 (2H, d, J=8.2 Hz); 7.23-7.54 (7H, m); 7.76 (2H, d, J=8.5 Hz); 11.77 (1H, s).

후처리

  1. additionwas added
  2. extractionThe ethyl acetate extract
  3. washwas washed with water (50 ml), brine (30 ml)
  4. dry with materialdried (Na2SO4)
  5. customThe solvent was evaporated
  6. dissolutionthe residue was dissolved in a small amount of benzene (0.5-1 ml)
  7. filtrationThe precipitated solid was filtered off
  8. customthe filtrate was evaporated
  9. customchromatographed on silicagel (10 g) with benzene-ethyl acetate (9:1) as eluent

출처 및 근거

ORD 기록
ord-14aae1f8dfb841ce930c6398aee0f0e2
출처 데이터셋
uspto-grants-2008_12
특허 번호
US07465719B2

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