1-Dimethylsulfamoyl-2-t-butyldimethylsilyl-5-imidazolecarboxaldehyde → 2-(Tert-butyl-dimethyl-silanyl)-5-{[4-(tert-butyl-dimethyl-silanyloxy)-thiochroman-6-yl]-hydroxy-methyl}-imidazole-1-sulfonic acid dimethylamide

HRID 747286Notes

Reaction equation

HRID 747286 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[S:8][CH2:7][CH2:6][CH:5]2[O:12][Si:13]([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:15])[CH3:14].[Li]CCCC.[CH3:25][N:26]([CH3:44])[S:27]([N:30]1[C:34]([CH:35]=[O:36])=[CH:33][N:32]=[C:31]1[Si:37]([C:40]([CH3:43])([CH3:42])[CH3:41])([CH3:39])[CH3:38])(=[O:29])=[O:28]>C1COCC1>[CH3:25][N:26]([CH3:44])[S:27]([N:30]1[C:34]([CH:35]([C:2]2[CH:3]=[C:4]3[C:9](=[CH:10][CH:11]=2)[S:8][CH2:7][CH2:6][CH:5]3[O:12][Si:13]([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:15])[CH3:14])[OH:36])=[CH:33][N:32]=[C:31]1[Si:37]([C:40]([CH3:42])([CH3:41])[CH3:43])([CH3:39])[CH3:38])(=[O:28])=[O:29]

Participants

5

Reactant 3

HCID 99959681-Dimethylsulfamoyl-2-t-butyldimethylsilyl-5-imidazolecarboxaldehydeHCID 59749549(6-Bromo-thiochroman-4-yl-oxy)-tert-butyl-dimethyl-silaneHCID 178418339Butyllithium

Product 1

HCID 597495632-(Tert-butyl-dimethyl-silanyl)-5-{[4-(tert-butyl-dimethyl-silanyloxy)-thiochroman-6-yl]-hydroxy-methyl}-imidazole-1-sulfonic acid dimethylamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of (6-bromo-thiochroman-4-yl-oxy)-tert-butyl-dimethyl-silane (Intermediate-K3) (2.74 g, 7.64 mmol) in TH F (30 mL) was treated with nBuLi (3.1 mL of a 2.5 M soln) at −78° C. for 30 m. A solution of 2-(tert-butyl-dimethyl-silanyl)-5-formyl-imidazole-1-sulfonic acid dimethylamide (see the General Method above, Intermediate K1) (2.42 g, 7.63 mmol) in THF (10 mL) was added via cannula. After 15 m, the reaction mixture was allowed to warm to rt for 16 h. The mixture was quenched with water, washed with brine and dried over Na2SO4. The solvent was removed and the residue was purified by chromatography on silica gel with 20% EtOAc:hexane to afford 2-(tert-butyl-dimethyl-silanyl)-5-{[4-(tert-butyl-dimethyl-silanyloxy)-thiochroman-6-yl]-hydroxy-methyl}-imidazole-1-sulfonic acid dimethylamide (Intermediate K4) as an oil, 4.12 g.

Workup

  1. additionwas added via cannula
  2. customThe mixture was quenched with water
  3. washwashed with brine
  4. dry with materialdried over Na2SO4
  5. customThe solvent was removed
  6. customthe residue was purified by chromatography on silica gel with 20% EtOAc

Sources & evidence

ORD record
ord-cc33e6bf1843443fae36a0024a9ce4f9
Source dataset
uspto-grants-2008_07
Patent number
US07396849B2

Reaction notes

Loading…