Potassium Carbonate → HCID 54677070, compound

HRID 23518Notes

Reaction equation

HRID 23518 reaction equation
[OH:1][C:2]1[CH2:3][C:4]([CH2:12][CH2:13][C:14]2[N:15]=[C:16]([NH:19][C:20](=[O:22])[CH3:21])[S:17][CH:18]=2)([CH:9]([CH3:11])[CH3:10])[O:5][C:6](=[O:8])[CH:7]=1.[C:23]([C:27]1[CH:32]=[C:31]([CH2:33][OH:34])[C:30]([CH3:35])=[CH:29][C:28]=1[S:36]S(C1C=CC(C)=CC=1)(=O)=O)([CH3:26])([CH3:25])[CH3:24].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[C:23]([C:27]1[CH:32]=[C:31]([CH2:33][OH:34])[C:30]([CH3:35])=[CH:29][C:28]=1[S:36][C:7]1[C:6](=[O:8])[O:5][C:4]([CH2:12][CH2:13][C:14]2[N:15]=[C:16]([NH:19][C:20](=[O:22])[CH3:21])[S:17][CH:18]=2)([CH:9]([CH3:11])[CH3:10])[CH2:3][C:2]=1[OH:1])([CH3:26])([CH3:25])[CH3:24]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 10499026S-[2-Tert-butyl-4-(hydroxymethyl)-5-methylphenyl] 4-methylbenzenesulfonothioateHCID 54713486N-{4-[2-(4-hydroxy-2-isopropyl-6-oxo-3,6-dihydro-2H-pyran-2-yl)-ethyl]-thiazol-2-yl}-acetamide

Product 1

HCID 54677070HCID 54677070, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The title compound was prepared according to General Method 16a using N-{4-[2-(4-hydroxy-2-isopropyl-6-oxo-3,6-dihydro-2H-pyran-2-yl)-ethyl]-thiazol-2-yl}-acetamide (Example E-13; 0.49 g, 1.5 mmol), toluene-4-thiosulfonic acid S-(2-tert-butyl-4-hydroxymethyl-5-methyl-phenyl)ester (Example BB-2; 0.66 g, 1.8 mmol), potassium carbonate (0.83 g, 6.0 mmol), and DMF (5 mL). The product was chromatographed on silica gel, eluting with 5% MeOH in CH2Cl2, to give the title compound, mp 128-130° 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-cd3184cc903b4e5fb85c2e10ee193264
Source dataset
uspto-grants-2005_02
Patent number
US06852711B2

Reaction notes

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