Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)- → HCID 136381722, compound

HRID 968845Notes

Reaction equation

HRID 968845 reaction equation
[C:1]([C:4]([CH3:35])([O:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][CH2:14][CH2:15][C:16]([NH:18][N:19]([CH2:26][C:27]2[CH:32]=[CH:31][C:30]([Cl:33])=[C:29]([Cl:34])[CH:28]=2)[C:20]([NH:22]CCC)=[O:21])=O)=[CH:9][CH:8]=1)[CH3:5])([OH:3])=[O:2].C12(CS(O)(=O)=O)C(C)(C)C(CC1)CC2=O>C1(C)C=CC=CC=1>[Cl:34][C:29]1[CH:28]=[C:27]([CH:32]=[CH:31][C:30]=1[Cl:33])[CH2:26][N:19]1[C:20](=[O:21])[NH:22][C:16]([CH2:15][CH2:14][CH2:13][C:10]2[CH:11]=[CH:12][C:7]([O:6][C:4]([CH3:35])([CH3:5])[C:1]([OH:3])=[O:2])=[CH:8][CH:9]=2)=[N:18]1

Participants

4

Reactant 2

HCID 18462Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)-HCID 59015940HCID 59015940, compound

Product 1

HCID 136381722HCID 136381722, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
90 °C

Procedure

To substrate 1-[4-[4-(1-Carboxy-1-methylethoxy)-phenyl]butyryl]-2-(3,4-dichlorophenylmethyl)-4-(propyl)semicarbazide (0.3658 g, 0.697 mmol) and camphorsulfonic acid (0.1658 g, 0.714 mmol) was added toluene (10 mL) and the resulting solution heated to 90° C. for 1 h. The solution was concentrated to an oil, and chromatographed on silica gel (7:3 ethyl acetate:hexanes) to afford title compound as an oil (0.2397 g, 0.473 mmol, 68%): 1H NMR (DMSO-d6) δ 12.95 (br s, 1 H), 7.58 (d, 2 H, J=8 Hz), 7.46 (d, 1 H, J=1.5 Hz), 7.19 (dd, 1 H, J=8, 1.5 Hz), 7.03 (d, 2 H, J=8.5 Hz), 6.72 (d, 2 H, J=8.5 Hz), 4.85 (s, 2 H), 3.47 (t, 2 H, J=7 Hz), 2.54 (t, 2 H, J=7.5 Hz), 1.83 (m, 2 H), 1.52 (q, 2 H, J=7 Hz), 1.45 (s, 6 H), 0.79 (t, 3 H, J=7 Hz); 13C NMR (DMSO-d6) δ 175.8, 154.1, 147.3, 139.2, 135.2, 131.7, 131.5, 130.8, 130.1, 129.7, 128.4, 119.3, 79.0, 47.3, 42.9, 34.0, 27.8, 25.7, 24.8, 22.5, 11.5; IR (CHCl3) 3028, 3005, 2939, 2878, 1696, 1574, 1509, 1472 cm−1; Anal. Calcd. for C25H29Cl2N3O4: C, 59.29; H, 5.77; N, 8.30. Found: C, 59.33; H, 5.63; N, 8.10.

Workup

  1. concentrationThe solution was concentrated to an oil
  2. customchromatographed on silica gel (7:3 ethyl acetate:hexanes)

Sources & evidence

ORD record
ord-905ef01c860d425da0b24c82fb8edec7
Source dataset
uspto-grants-2007_12
Patent number
US07304062B2

Reaction notes

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