Potassium Carbonate → N-[5-tert-butyl-4-[[4-hydroxy-2-[2-(4-hydroxyphenyl)ethyl]-2-methyl-6-oxo-3H-pyran-5-yl]sulfanyl]-2-methyl-phenyl]-4-cyano-benzenesulfonamide

HRID 356542Notes

Reaction equation

HRID 356542 reaction equation
[OH:1][C:2]1[CH2:7][C:6]([CH2:9][CH2:10][C:11]2[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=2)([CH3:8])[O:5][C:4](=[O:18])[CH:3]=1.C([O-])([O-])=O.[K+].[K+].[C:25]([C:29]1[CH:34]=[C:33]([NH:35][S:36]([C:39]2[CH:44]=[CH:43][C:42]([C:45]#[N:46])=[CH:41][CH:40]=2)(=[O:38])=[O:37])[C:32]([CH3:47])=[CH:31][C:30]=1[S:48]S(C1C=CC(C)=CC=1)(=O)=O)([CH3:28])([CH3:27])[CH3:26]>CN(C=O)C>[C:25]([C:29]1[C:30]([S:48][C:3]2[C:4](=[O:18])[O:5][C:6]([CH2:9][CH2:10][C:11]3[CH:12]=[CH:13][C:14]([OH:17])=[CH:15][CH:16]=3)([CH3:8])[CH2:7][C:2]=2[OH:1])=[CH:31][C:32]([CH3:47])=[C:33]([NH:35][S:36]([C:39]2[CH:44]=[CH:43][C:42]([C:45]#[N:46])=[CH:41][CH:40]=2)(=[O:38])=[O:37])[CH:34]=1)([CH3:28])([CH3:27])[CH3:26]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 10673378Toluene-4-thiosulfonic acid S-[2-tert-butyl-4-(4-cyano-benzenesulfonylamino)-5-methyl-phenyl] esterHCID 546822784-Hydroxy-6-[2-(4-hydroxy-phenyl)-ethyl]-6-methyl-5,6-dihydro-pyran-2-one

Product 1

HCID 54682297N-[5-tert-butyl-4-[[4-hydroxy-2-[2-(4-hydroxyphenyl)ethyl]-2-methyl-6-oxo-3H-pyran-5-yl]sulfanyl]-2-methyl-phenyl]-4-cyano-benzenesulfonamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The title compound was prepared as described in General Method 9 from 4-hydroxy-6-[2-(4-hydroxy-phenyl)-ethyl]-6-methyl-5,6-dihydro-pyran-2-one (prepared in Example KK; 0.09 g, 0.37 mmol), DMF (6 mL), K2CO3 (0.11 g, 0.81 mmol), and toluene-4-thiosulfonic acid S-[2-tert-butyl-4-(4-cyano-benzenesulfonylamino)-5-methyl-phenyl] ester (prepared in Example JJJJ; 0.19 g, 0.37 mmol). The mixture was stirred at room temperature overnight. After the standard work-up, the resulting residue was flash chromatographed on silica gel, eluting with 2% EtOH:EtOAc, then triturated with EtOAc:CH2Cl2 :hexanes to afford the title compound. 1H NMR (DMSO-d6) δ 1.24 (s, 9 H), 1.42 (s, 3 H), 1.87 (s, 3 H), 1.92 (m, 2 H), 2.52 (m, partially obscured by DMSO, 2 H), 2.75 (d of ABX q, 1 H), 2.95 (d of ABX q, 1 H), 6.46 (s, 1 H), 6.64 (d, 2 H), 6.70 (s, 1 H), 6.96 (d, 2 H), 7.77 (d, 2 H), 8.06 (d, 2 H), 9.15 (s, 1 H), 9.68 (s, 1 H).

Workup

  1. customThe title compound was prepared
  2. customchromatographed on silica gel
  3. washeluting with 2% EtOH
  4. customEtOAc, then triturated with EtOAc

Sources & evidence

ORD record
ord-6298182238cc4f89a3cadd3f0336aaa6
Source dataset
uspto-grants-1998_11
Patent number
US05834506

Reaction notes

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