p-Toluenesulfonic acid → HCID 178466789, compound

HRID 1717795Notes

Reaction equation

HRID 1717795 reaction equation
[OH:1][C:2]1[C:7]([CH3:8])=[C:6]([O:9][CH2:10][C:11]2[CH:16]=[CH:15][C:14]([CH:17]([C:25]3[CH:30]=[CH:29][CH:28]=[C:27]([C:31]4[NH:35][C:34]([SH:36])=[N:33][N:32]=4)[CH:26]=3)[O:18]C3CCCCO3)=[CH:13][CH:12]=2)[CH:5]=[CH:4][C:3]=1[C:37](=[O:39])[CH3:38].C1(C)C=CC(S(O)(=O)=O)=CC=1>CO.C(OCC)(=O)C>[OH:1][C:2]1[C:7]([CH3:8])=[C:6]([O:9][CH2:10][C:11]2[CH:16]=[CH:15][C:14]([CH:17]([OH:18])[C:25]3[CH:30]=[CH:29][CH:28]=[C:27]([C:31]4[NH:35][C:34]([SH:36])=[N:33][N:32]=4)[CH:26]=3)=[CH:13][CH:12]=2)[CH:5]=[CH:4][C:3]=1[C:37](=[O:39])[CH3:38]

Participants

5

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 178466790HCID 178466790, compound

Product 1

HCID 178466789HCID 178466789, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

Stir a solution of 1-(2-hydroxy-4-{4-[[3-(5-mercapto-4H-[1,2,4]triazol-3-yl)-phenyl]-(tetrahydro-pyran-2-yloxy)-methyl]-benzyloxy}-3-methyl-phenyl)-ethanone (1.12 g, 2.04 mmol) and p-toluenesulfonic acid (50 mg) in methanol (0.2M). Dilute with ethyl acetate and wash with water. Dry the organic layer and concentrate to afford the title compound (0.250 g, 0.551 mmol, 27% overall from acid chloride). 1H NMR (400 MHz, DMSO-d6) δ 2.02 (s, 3H), 2.50 (s, 3H), 5.21 (s, 2H), 5.76 (s, 1H), 6.05 (s, 1H), 6.71 (d, J=9.4 Hz, 1H), 7.39 (m, 6H), 7.53 (m, 1H), 7.73 (m, 1H), 7.78 (d, J=9.0 Hz, 1H), 7.98 (s, 1H), 12.83 (s, 1H). MS (m/z): 460 (M−H).

Workup

  1. washwash with water
  2. customDry the organic layer
  3. concentrationconcentrate

Sources & evidence

ORD record
ord-5df27a85e2fa4b298bfff922bb6ae59e
Source dataset
uspto-grants-2010_09
Patent number
US07803938B2

Reaction notes

Loading…