Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)- → HCID 57608552, compound

HRID 968858Notes

Reaction equation

HRID 968858 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]([CH2:26][C:27]2[CH:32]=[CH:31][C:30]([C:33]([CH3:36])([CH3:35])[CH3:34])=[CH:29][CH:28]=2)[C:22]([NH:24][CH3:25])=[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>[CH2:1]([O:3][C:4](=[O:5])[C:6]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][CH2:17][C:18]2[N:24]([CH3:25])[C:22](=[O:23])[N:21]([CH2:26][C:27]3[CH:32]=[CH:31][C:30]([C:33]([CH3:36])([CH3:35])[CH3:34])=[CH:29][CH:28]=3)[N:20]=2)=[CH:11][CH:10]=1)([CH3:37])[CH3:7])[CH3:2]

Participants

4

Reactant 2

HCID 18462Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)-HCID 59016052HCID 59016052, compound

Product 1

HCID 57608552HCID 57608552, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

1-[4-[4-(1-Ethoxycarbonyl-1-methylethoxy)phenyl]butyryl]-2-(4-t-butyl phenylmethyl)-4-methylsemicarbazide (0.93 g, 1.82 mmol) was dissolved in ethyl acetate (10 mL). Camphorsulfonic acid (0.46 g, 1.98 mmol) was added in one portion and the solution was heated to reflux and stirred for 1 h. The solution was cooled to rt and washed with sat'd aq. NaHCO3 (2×8 mL), 1N HCl (2×8 mL) and sat'd aq. NaCl (8 mL)). The organic phase was dried (MgSO4), filtered and concentrated to afford the title compound as clear, colorless oil (0.84 g, 93.6%): 1H NMR (DMSO-d6) δ 7.30 (d, 2H, J=8 Hz), 7.15 (d, 2H, J=8 Hz), 7.05 (d, 2H, J=8 Hz), 6.68 (d, 2H, J=8 Hz), 4.77 (s, 2H), 4.13 (q, 2H, J=7 Hz), 3.69 (s, 3H), 2.53 (t, 2H, J=8 Hz), 2.47 (t, 2H, J=8 Hz), 1.81 (quint, 2H, J=7 Hz), 1.47 (s, 6H), 1.22 (s, 9H), 1.14 (t, 3H, J=7 Hz); 13C NMR (DMSO-d6) δ 174.0, 154.1, 153.8, 150.4, 147.1, 135.6, 135.0, 129.8, 128.0, 125.9, 119.5, 79.2, 61.6, 48.3, 34.9, 34.1, 31.8, 27.7, 27.6, 25.7, 25.1, 14.6; IR *(CHCl3) 2967, 1695, 1509, 1475, 1232 cm−1; Anal. Calcd. for C29H39N3O4: C, 70.56; H, 7.96; N, 8.51. Found: C, 70.28; H, 7.85; N, 8.43.

Workup

  1. temperaturethe solution was heated
  2. temperatureto reflux
  3. washwashed with sat'd aq. NaHCO3 (2×8 mL), 1N HCl (2×8 mL)
  4. dry with materialThe organic phase was dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-7d1fd20a8fb74fcd93fb020d26865e4d
Source dataset
uspto-grants-2007_12
Patent number
US07304062B2

Reaction notes

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