Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)- → HCID 59015888, compound

HRID 968850Notes

Reaction equation

HRID 968850 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]([CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[C:22]([NH:24][CH2:25][CH2:26][CH3:27])=[O:23])=[O:19])=[CH:11][CH:10]=1)[CH3:7])=[O:5])[CH3:2].C(OC(=O)C(OC1C=CC(CCCC2N(CCC)C(=O)N(CC3C=CC=CC=3)N=2)=CC=1)(C)C)C.C12(CS(O)(=O)=O)C(C)(C)C(CC1)CC2=O>C(OCC)(=O)C>[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]([CH2:28][C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=2)[C:22]([NH:24][CH2:25][CH2:26][CH3:27])=[O:23])=[O:19])=[CH:11][CH:10]=1)[CH3:7])=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 18462Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)-HCID 86628490HCID 86628490, compound

Product 1

HCID 59015888HCID 59015888, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

2-{4-[3-(1-Phenylmethyl-5-oxo-4-propyl-4,5-dihydro-1H-[1,2,4]triazol-3-yl)-propyl]-phenoxy}-2-methylpropionic acid ethyl ester 1-[4-[4-(1-Ethoxycarbonyl-1-methylethoxy)phenyl]butyryl]-2-phenylmethyl-4-(propyl)semicarbazide (1.26 g, 2.61 mmol) was dissolved in ethyl acetate (15 mL). Camphorsulfonic acid (670 mg, 2.88 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(2×10 mL) followed by 1N HCl (2×10 mL). The organic phase was dried (MgSO4) and concentrated to a clear, colorless oil. The material was purified by plug silica gel filtration (gradient dichloromethane to ethyl acetate) to afford the title compound as a clear, colorless oil (0.86 g, 71%). 1H NMR (DMSO-d6) □ 7.30 (t, 3H, J=7 Hz), 7.24 (d, 1H, J=7 Hz), 7.20 (d, 2H, J=7 Hz ), 7.04 (d, 2H, J=8 Hz), 6.69 (d, 2H, J=8 Hz), 4.13 (q, 2H, J=7 Hz), 3.47 (t, 2H, J=7 Hz), 2.55 (t, 2H, J=7 Hz), 2.48 (t, 2H, J=7 Hz), 1.83 (quint, 2H, J=7 Hz), 1.52, (m, 2H), 1.47 (s, 6H), 1.14 (t, 3H, J=7 Hz), 0.79 (t, 3H, J=7 Hz); 13C NMR (DMSO-d6) □ 174.0, 154.1, 153.8, 146.9, 138.1, 135.6, 129.8, 129.1, 128.0, 119.6, 79.3, 61.6, 48.5, 42.8, 34.0, 27.8, 25.7, 24.8, 22.5, 14.5, 11.5; IR (CHCl13) 2878, 1692, 1509, 1143 cm−1; Anal. Calcd. For C27H35N304: C, 69.65; H, 7.58; N, 9.03. Found: C, 69.28; H, 7.96; N, 8.84.

Workup

  1. temperaturethe solution was heated
  2. temperatureto reflux for 1 h
  3. washwashed with sat'd aq. NaHCO3(2×10 mL)
  4. dry with materialThe organic phase was dried (MgSO4)
  5. concentrationconcentrated to a clear, colorless oil
  6. filtrationThe material was purified by plug silica gel filtration (gradient dichloromethane to ethyl acetate)

Sources & evidence

ORD record
ord-32eb6df6b53443d8b1eb2d0437fe6994
Source dataset
uspto-grants-2007_12
Patent number
US07304062B2

Reaction notes

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