HCID 86591039, compound → 2-(2,4-Dimethoxy-benzyl)-5-(5-(1-hydroxy-4-methyl-pentyl)-thiophen-2-ylmethyl]-1,1-dioxo-1,2,5-thiadiazolidin-3-one

HRID 1592003Notes

Reaction equation

HRID 1592003 reaction equation
[CH3:1][O:2][C:3]1[CH:25]=[C:24]([O:26][CH3:27])[CH:23]=[CH:22][C:4]=1[CH2:5][N:6]1[S:10](=[O:12])(=[O:11])[N:9]([CH2:13][C:14]2[S:18][C:17]([CH:19]=[O:20])=[CH:16][CH:15]=2)[CH2:8][C:7]1=[O:21].[CH2:28]([Mg]Br)[CH2:29][CH:30]([CH3:32])[CH3:31]>C1COCC1>[CH3:1][O:2][C:3]1[CH:25]=[C:24]([O:26][CH3:27])[CH:23]=[CH:22][C:4]=1[CH2:5][N:6]1[C:7](=[O:21])[CH2:8][N:9]([CH2:13][C:14]2[S:18][C:17]([CH:19]([OH:20])[CH2:28][CH2:29][CH:30]([CH3:32])[CH3:31])=[CH:16][CH:15]=2)[S:10]1(=[O:12])=[O:11]

Participants

4

Reactant 2

HCID 86591039HCID 86591039, compoundHCID 178418529HCID 178418529, compound

Product 1

HCID 671386072-(2,4-Dimethoxy-benzyl)-5-(5-(1-hydroxy-4-methyl-pentyl)-thiophen-2-ylmethyl]-1,1-dioxo-1,2,5-thiadiazolidin-3-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-70 °C

Procedure

A solution of the title B compound, 5-[5-(2,4-dimethoxy-benzyl)-1,1,4-trioxo-1,2,5-thiadiazolidin-2-ylmethyl]-thiophene-2-carbaldehyde (545 mg, 1.33 mmol) in dry THF (8 mL) is added dropwise to a cold (−70° C.) solution of isopentylmagnesium bromide (2.22 mmol) in dry THF (10 mL) keeping the temperature below −65° C. The mixture is stirred at −70° C. for 45 min and the reaction is quenched with saturated aqueous NH4Cl solution. The mixture is diluted with EtOAc and the layers are separated. The organic layer is dried over anhydrous MgSO4 and the solvent is evaporated. The residue is chromatographed on silica gel using 0→100% EtOAc in hexane as the eluent to afford 2-(2,4-dimethoxy-benzyl)-5-(5-(1-hydroxy-4-methyl-pentyl)-thiophen-2-ylmethyl]-1,1-dioxo-1,2,5-thiadiazolidin-3-one a yellow oil: [M+NH4]+=500.

Workup

  1. customthe temperature below −65° C
  2. customthe reaction is quenched with saturated aqueous NH4Cl solution
  3. additionThe mixture is diluted with EtOAc
  4. customthe layers are separated
  5. dry with materialThe organic layer is dried over anhydrous MgSO4
  6. customthe solvent is evaporated
  7. customThe residue is chromatographed on silica gel using 0→100% EtOAc in hexane as the eluent

Sources & evidence

ORD record
ord-a930d3d4307044a98efef3429c42aeb5
Source dataset
uspto-grants-2007_11
Patent number
US07291635B2

Reaction notes

Loading…