p-Toluenesulfonic acid → HCID 57884432, compound

HRID 1818540Notes

Reaction equation

HRID 1818540 reaction equation
Cl[CH2:2][C:3]([C:5]1[CH:6]=[C:7]([CH:11]([O:32]C2CCCCO2)[C:12]2[CH:31]=[CH:30][C:15]([CH2:16][O:17][C:18]3[CH:23]=[CH:22][C:21]([C:24](=[O:27])[CH2:25][CH3:26])=[C:20]([OH:28])[C:19]=3[CH3:29])=[CH:14][CH:13]=2)[CH:8]=[CH:9][CH:10]=1)=O.[S-:39][C:40]#[N:41].[K+].C1(C)C=CC(S(O)(=O)=[O:50])=CC=1>C(O)C>[OH:32][CH:11]([C:12]1[CH:13]=[CH:14][C:15]([CH2:16][O:17][C:18]2[CH:23]=[CH:22][C:21]([C:24](=[O:27])[CH2:25][CH3:26])=[C:20]([OH:28])[C:19]=2[CH3:29])=[CH:30][CH:31]=1)[C:7]1[CH:6]=[C:5]([C:3]2[NH:41][C:40](=[O:50])[S:39][CH:2]=2)[CH:10]=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 516872Potassium thiocyanateHCID 57438380HCID 57438380, compound

Product 1

HCID 57884432HCID 57884432, compoundYield 308.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Heat a solution of 1-(4-{4-[[3-(2-chloro-acetyl)-phenyl]-(tetrahydro-pyran-2-yloxy)-methyl]-benzyloxy}-2-hydroxy-3-methyl-phenyl)-propan-1-one (0.250 mg, 0.466 mmol) and potassium thiocyanate (90.5 mg, 0.931 mmol) in ethanol (0.20 M) overnight at 70° C. Add p-toluenesulfonic acid (10 mg) and stir overnight. Evaporate solvents and chromatograph residue. Major fraction isolated was the title compound (0.086 g, 0.179 mmol, 39%): 1H NMR (400 MHz, DMSO-d6) δ 1.09 (t, J=7.2 Hz, 3H), 2.02 (s, 3H), 3.03 (q, J=9.6 Hz, 2H), 5.10 (s, 2H), 5.20 (s, 2H), 5.82 (d, J=3.9 Hz, 1H), 6.11 (d, J=3.9 Hz, 1H), 6.70 (d, J=9.0 Hz, 1H), 7.42 (q, J=11.2 Hz, 4H), 7.51 (t, J=7.8 Hz, 1H), 7.71 (d, J=7.8 Hz, 1H), 7.81 (d, J=9.0 Hz, 1H), 7.87 (d, J=8.2 Hz, 1H), 8.04 (s, 1H), 12.88 (s, 1H). MS (m/z): 474 (M−H).

Workup

  1. customMajor fraction isolated

Sources & evidence

ORD record
ord-126f8ed59f6541b1b8f1cd83a764080d
Source dataset
uspto-grants-2009_10
Patent number
US07598423B2

Reaction notes

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