p-Toluenesulfonic acid → HCID 57884414, compound

HRID 1818541Notes

Reaction equation

HRID 1818541 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.[NH2:39][C:40]([NH2:42])=[S:41].C1(C)C=CC(S(O)(=O)=O)=CC=1>C(O)C>[NH2:42][C:40]1[S:41][CH:2]=[C:3]([C:5]2[CH:6]=[C:7]([CH:11]([OH:32])[C:12]3[CH:31]=[CH:30][C:15]([CH2:16][O:17][C:18]4[CH:23]=[CH:22][C:21]([C:24](=[O:27])[CH2:25][CH3:26])=[C:20]([OH:28])[C:19]=4[CH3:29])=[CH:14][CH:13]=3)[CH:8]=[CH:9][CH:10]=2)[N:39]=1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 2723790ThioureaHCID 57438380HCID 57438380, compound

Product 1

HCID 57884414HCID 57884414, compoundYield 52.1%

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 thiourea (71 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 (0.115 g, 0.243 mmol, 52%): 1H NMR (400 MHz, DMSO-d6) δ 1.09 (t, J=10.5 Hz, 3H), 2.02 (s, 3H), 3.03 (q, J=14.4 Hz, 2H), 5.20 (s, 2H), 5.75 (s, 1H), 6.70 (d, J=9.0 Hz, 1H), 7.14 (s, 1H), 7.37 (d, J=6.43 Hz, 1H), 7.42 (m, 6H), 7.60 (m, 1H), 7.80 (m, 2H), 12.89 (s, 1H). MS (m/z): 473 (M−H).

Workup

  1. customMajor fraction isolated

Sources & evidence

ORD record
ord-714c47d288da42659a712a48441a2ace
Source dataset
uspto-grants-2009_10
Patent number
US07598423B2

Reaction notes

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