Potassium Carbonate → 5-[2-tert-butyl-4-(hydroxymethyl)-5-methyl-phenyl]sulfanyl-4-hydroxy-2-isopropyl-2-[2-(4-methylthiazol-2-yl)ethyl]-3H-pyran-6-one

HRID 23517Notes

Reaction equation

HRID 23517 reaction equation
[OH:1][C:2]1[CH2:7][C:6]([CH:16]([CH3:18])[CH3:17])([CH2:8][CH2:9][C:10]2[S:11][CH:12]=[C:13]([CH3:15])[N:14]=2)[O:5][C:4](=[O:19])[CH:3]=1.[C:20]([C:24]1[CH:29]=[C:28]([CH2:30][OH:31])[C:27]([CH3:32])=[CH:26][C:25]=1[S:33]S(C1C=CC(C)=CC=1)(=O)=O)([CH3:23])([CH3:22])[CH3:21].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[C:20]([C:24]1[CH:29]=[C:28]([CH2:30][OH:31])[C:27]([CH3:32])=[CH:26][C:25]=1[S:33][C:3]1[C:4](=[O:19])[O:5][C:6]([CH:16]([CH3:17])[CH3:18])([CH2:8][CH2:9][C:10]2[S:11][CH:12]=[C:13]([CH3:15])[N:14]=2)[CH2:7][C:2]=1[OH:1])([CH3:23])([CH3:22])[CH3:21]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 10499026S-[2-Tert-butyl-4-(hydroxymethyl)-5-methylphenyl] 4-methylbenzenesulfonothioateHCID 547027824-Hydroxy-6-isopropyl-6-[2-(4-methyl-thiazol-2-yl)-ethyl]-5,6-dihydro-pyran-2-one

Product 1

HCID 546770195-[2-tert-butyl-4-(hydroxymethyl)-5-methyl-phenyl]sulfanyl-4-hydroxy-2-isopropyl-2-[2-(4-methylthiazol-2-yl)ethyl]-3H-pyran-6-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The title compound was prepared according to General Method 16a using 4-hydroxy-6-isopropyl-6-[2-(4-methyl-thiazol-2-yl)-ethyl]-5,6-dihydro-pyran-2-one (Example E-6; 0.33 g, 1.2 mmol), toluene-4-thiosulfonic acid S-(2-tert-butyl-4-hydroxymethyl-5-methyl-phenyl)ester (Example BB-2; 0.51 g, 1.4 mmol), potassium carbonate (0.48 g, 3.5 mmol), and DMF (5 mL). The product was chromatographed on silica gel, eluting with 5% MeOH in CH2Cl2, to give the title compound, mp 98-100° C.

Workup

  1. customThe title compound was prepared
  2. customThe product was chromatographed on silica gel
  3. washeluting with 5% MeOH in CH2Cl2

Sources & evidence

ORD record
ord-e42c3b4fcb084e90a74d5dec11a8616f
Source dataset
uspto-grants-2005_02
Patent number
US06852711B2

Reaction notes

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