Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)- → HCID 136368693, compound

HRID 968855Notes

Reaction equation

HRID 968855 reaction equation
[CH2:1]([O:3][C:4]([C:6]([CH3:35])([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]([CH3:33])=[C:29]([CH3:34])[CH:28]=2)[C:22]([NH:24]C)=[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[NH:24][C:22](=[O:23])[N:21]([CH2:26][C:27]3[CH:32]=[CH:31][C:30]([CH3:33])=[C:29]([CH3:34])[CH:28]=3)[N:20]=2)=[CH:11][CH:10]=1)([CH3:35])[CH3:7])[CH3:2]

Participants

4

Reactant 2

HCID 18462Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)-HCID 59016005HCID 59016005, compound

Product 1

HCID 136368693HCID 136368693, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

1-[4-[4-(1-Ethoxycarbonyl-1-methylethoxy)phenyl]butyryl]-2-(3,4-dimethylphenylmethyl)-4-methylsemicarbazide (1.20 g, 2.47 mmol) was dissolved in ethyl acetate (10 mL). Camphorsulfonic acid (0.64 g, 2.72 mmol) was added in one portion and the solution was heated to reflux for 1 h. The solution was cooled to rt and washed with sat'd aq. NaHCO3 (2×8 mL) followed by 1H HCl (2×8 mL ). The organic phase was dried (MgSO4) and concentrated to afford the title compound as a clear, colorless oil (1.08 g, 94%). 1H NMR (DMSO-d6) δ 7.04 (m, 3H), 7.03 (s, 1H), 6.93 (d, 1H, J=2 Hz), 6.68 (d, 2H, J=7 Hz), 4.72 (s, 2H), 4.13 (q, 2H, J=7 Hz), 3.08 (s, 3H), 2.53 (t, 2H, J=8 Hz), 2.47 (t, 2H, J=8 Hz), 1.80 (quint, 2H, J=7 Hz), 1.47 (s, 6H), 1.14 (t, 3H, J=7 Hz); 13C NMR (DMSO-d6) δ 174.0, 154.1, 147.1, 136.8, 135.9, 135.6, 135.3, 130.1, 129.8, 129.4, 125.7, 119.5, 79.2, 61.6, 48.4, 34.1, 27.7, 27.6, 25.7, 25.0, 20.0, 19.7, 14.6; IR (CHCl3) 2941, 1729, 1509, 1238, 1143 cm−1; Anal. Calcd. for C27H35N3O4: C, 69.65; H, 7.58; N, 9.03. Found: C, 69.25; H, 7.47; N, 8.88.

Workup

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

Sources & evidence

ORD record
ord-ad03023c38114f6f9278849d5f41da29
Source dataset
uspto-grants-2007_12
Patent number
US07304062B2

Reaction notes

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