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

HRID 2375236Notes

Reaction equation

HRID 2375236 reaction equation
[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

Participants

6

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-14aae1f8dfb841ce930c6398aee0f0e2
Source dataset
uspto-grants-2008_12
Patent number
US07465719B2

Reaction notes

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