p-Toluenesulfonic acid → HCID 178466789, compound

HRID 1161108Notes

Reaction equation

HRID 1161108 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-4e3425d1de2b4e35ae5c370a418fef8d
Source dataset
uspto-grants-2010_10
Patent number
US07816523B2

Reaction notes

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