Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)- → HCID 136381723, compound

HRID 968846Notes

Reaction equation

HRID 968846 reaction equation
[CH2:1]([O:3][C:4]([C:6]([CH3:37])([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][CH2:17][C:18]([NH:20][N:21]([CH2:28][C:29]2[CH:34]=[CH:33][C:32]([Cl:35])=[C:31]([Cl:36])[CH:30]=2)[C:22]([NH:24]CCC)=[O:23])=O)=[CH:11][CH:10]=1)[CH3:7])=[O:5])[CH3:2].C12(CS(O)(=O)=O)C(C)(C)C(CC1)CC2=O>C(OCC)(=O)C>[Cl:36][C:31]1[CH:30]=[C:29]([CH:34]=[CH:33][C:32]=1[Cl:35])[CH2:28][N:21]1[C:22](=[O:23])[NH:24][C:18]([CH2:17][CH2:16][CH2:15][C:12]2[CH:13]=[CH:14][C:9]([O:8][C:6]([CH3:37])([CH3:7])[C:4]([O:3][CH2:1][CH3:2])=[O:5])=[CH:10][CH:11]=2)=[N:20]1

Participants

4

Reactant 2

HCID 18462Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)-HCID 59015886HCID 59015886, compound

Product 1

HCID 136381723HCID 136381723, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

To substrate 1-[4-[4-(1-Ethoxycarbonyl-1-methylethoxy)phenyl]butyryl]-2-(3,4-dichlorophenylmethyl)-4-(propyl)semicarbazide (0.4976 g, 0.901 mmol) and camphorsulfonic acid (0.2078 g, 0.895 mmol) was added ethyl acetate (10 mL) and the resulting solution heated to reflux for 12 h. The solution was diluted with ethyl acetate, then washed with sat'd aq. NaHCO3 followed by sat'd aq. NaCl. It was then dried (MgSO4), filtered and concentrated to afford the title compound as an oil (0.4532 g (0.848 mmol, 94%): 1H NMR (DMSO-d6) δ 7.59 (d, 1H, J=8.5 Hz), 7.47 (d, 1H, J=2 Hz), 7.19 (dd, 1H, J=8.5, 2 Hz), 7.03 (d, 2 H, J=8.5 Hz), 6.69 (d, 2H, J=8.5 Hz), 4.85 (s, 2H), 4.13 (q, 2H, J=7 Hz), 3.48 (t, 2H, J=8 Hz), 2.55 (t, 2H, J=7 Hz), 1.83 (m, 2H), 1.52 (q, 2H, J=7 Hz), 1.47 (s, 6H), 1.14 (t, 3H, J=7 Hz), 0.79 (t, 3H, J=7 Hz); 13C NMR (DMSO-d6) δ 174.0, 154.1, 153.8, 147.3, 139.2, 135.6, 131.7, 131.5, 130.8, 130.1, 129.8, 128.4, 119.6, 79.3, 61.6, 47.3, 42.9, 34.0, 27.7, 25.7, 24.7, 22.4, 14.6, 11.5; IR (CHCl3) 3003, 2939, 1728, 1696, 1509 cm−1; HRMS calcd. for C27H34Cl2N3O4 (M+H)+: 524.1926. Found: 534.1935

Workup

  1. temperaturethe resulting solution heated
  2. temperatureto reflux for 12 h
  3. washwashed with sat'd aq. NaHCO3
  4. dry with materialIt was then dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-76769c104dbd4b21817f473a970061f7
Source dataset
uspto-grants-2007_12
Patent number
US07304062B2

Reaction notes

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