Imidazole → HCID 131733464, compound

HRID 2278375Notes

Reaction equation

HRID 2278375 reaction equation
[CH:1]([C:3]1[S:7][C:6]([C@H:8]([NH:11][S:12]([C:15]2[CH:23]=[CH:22][C:18]3[N:19]=[CH:20][S:21][C:17]=3[CH:16]=2)(=[O:14])=[O:13])[CH2:9][OH:10])=[CH:5][CH:4]=1)=[O:2].N1C=CN=C1.[CH3:29][C:30]([Si:33](Cl)([CH3:35])[CH3:34])([CH3:32])[CH3:31]>CN(C=O)C>[Si:33]([O:10][CH2:9][C@@H:8]([NH:11][S:12]([C:15]1[CH:23]=[CH:22][C:18]2[N:19]=[CH:20][S:21][C:17]=2[CH:16]=1)(=[O:14])=[O:13])[C:6]1[S:7][C:3]([CH:1]=[O:2])=[CH:4][CH:5]=1)([C:30]([CH3:32])([CH3:31])[CH3:29])([CH3:35])[CH3:34]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 117628891HCID 117628891, compound

Product 1

HCID 131733464HCID 131733464, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of N-[(1R)-1-(5-formylthiophen-2-yl)-2-hydroxyethyl]-1,3-benzothiazole-6-sulfonamide (5.48 g, 14.9 mmol) and imidazole (1.27 g, 18.6 mmol) in DMF (75 mL) was added TBSCl (2.80 g, 18.6 mmol) and the reaction mixture was stirred overnight. The reaction was then quenched by the addition of water (400 mL) and ether (200 mL). The phases were separated and the aqueous layer was extracted with ether (3×250 mL). The combined organic layers were washed twice with brine solution (2×300 mL), dried over magnesium sulfate, filtered and concentrated under reduced pressure. The crude was purified on silica gel eluting with hexanes and ethyl acetate to afford the title compound.

Workup

  1. customThe reaction was then quenched by the addition of water (400 mL) and ether (200 mL)
  2. customThe phases were separated
  3. extractionthe aqueous layer was extracted with ether (3×250 mL)
  4. washThe combined organic layers were washed twice with brine solution (2×300 mL)
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe crude was purified on silica gel eluting with hexanes and ethyl acetate

Sources & evidence

ORD record
ord-11a078d86b3d4853a9ba867a4f99b9dc
Source dataset
uspto-grants-2015_09
Patent number
US09133157B2

Reaction notes

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