Sodium Iodide → HCID 21094019, compound

HRID 729733Notes

Reaction equation

HRID 729733 reaction equation
[SH:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH2:17][CH:18]2[CH2:23][CH2:22][O:21][CH2:20][CH2:19]2)[C:9]([NH:11][C:12]2[S:13][CH:14]=[CH:15][N:16]=2)=[O:10])=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].[Na+].[I-].S(O[CH:43]1[CH2:46][O:45][CH2:44]1)(C1C=CC(C)=CC=1)(=O)=O>CC(N(C)C)=O>[O:45]1[CH2:46][CH:43]([S:1][C:2]2[CH:7]=[CH:6][C:5]([CH:8]([CH2:17][CH:18]3[CH2:23][CH2:22][O:21][CH2:20][CH2:19]3)[C:9]([NH:11][C:12]3[S:13][CH:14]=[CH:15][N:16]=3)=[O:10])=[CH:4][CH:3]=2)[CH2:44]1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 13153907Oxetan-3-yl 4-methylbenzene-1-sulfonateHCID 21093996HCID 21093996, compound

Product 1

HCID 21094019HCID 21094019, compound

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
130 °C

Procedure

A mixture of 2-(4-mercaptophenyl)-3-(tetrahydropyran-4-yl)-N-thiazol-2-ylpropionamide (see EXAMPLE 146, 349 mg, 1.0 mmol), K2CO3 (152 mg, 1.1 mmol), NaI (150 mg, 1.0 mmol), and 3-(tosyloxy)oxetane (274 mg, 1.2 mmol) in anhydrous DMAc (20 mL) was heated for 2 h at 130° C. The solvent was evaporated off under reduced pressure, then the residue was partitioned between CH2Cl2 (75 mL) and 2% aqueous citric acid (20 mL). The organic layer was washed with H2O (20 mL), saturated aqueous Na2CO3 (20 mL), and brine (20 mL), before being dried (MgSO4). Filtration and solvent evaporation afforded 2-[4-(oxetan-3-ylsulfanyl)phenyl]-3-(tetrahydropyran-4-yl)-N-thiazol-2-ylpropionamide: m/z (ES+)=405.2 [M+H]+. This thioether was oxidised employing the protocol outlined in EXAMPLE 148 to give the title compound: RTA=3.04 min; m/z (ES+)=437.2 [M+H]+.

Workup

  1. customThe solvent was evaporated off under reduced pressure
  2. customthe residue was partitioned between CH2Cl2 (75 mL) and 2% aqueous citric acid (20 mL)
  3. washThe organic layer was washed with H2O (20 mL), saturated aqueous Na2CO3 (20 mL), and brine (20 mL)
  4. dry with materialbefore being dried (MgSO4)
  5. filtrationFiltration and solvent evaporation

Sources & evidence

ORD record
ord-4c2442d3c85d46a99fb42311f22ca68c
Source dataset
uspto-grants-2009_09
Patent number
US07582632B2

Reaction notes

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