tert-Butyldimethylsilyl chloride → HCID 23614513, compound

HRID 1767952Notes

Reaction equation

HRID 1767952 reaction equation
[Si:1](Cl)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[CH3:9][C:10]1[N:11]=[C:12]([C:21]2[CH:26]=[CH:25][C:24]([C:27]([F:30])([F:29])[F:28])=[CH:23][CH:22]=2)[S:13][C:14]=1[CH:15]([OH:20])[CH2:16][CH2:17][CH2:18][OH:19]>N1C=CC=CC=1>[C:4]([Si:1]([CH3:3])([CH3:2])[O:19][CH2:18][CH2:17][CH2:16][CH:15]([C:14]1[S:13][C:12]([C:21]2[CH:26]=[CH:25][C:24]([C:27]([F:30])([F:29])[F:28])=[CH:23][CH:22]=2)=[N:11][C:10]=1[CH3:9])[OH:20])([CH3:7])([CH3:6])[CH3:5]

Participants

4

Reactant 2

HCID 28928tert-Butyldimethylsilyl chlorideHCID 236145121-{4-Methyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl}butane-1,4-diol

Product 1

HCID 23614513HCID 23614513, compoundYield 42.2%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

tert-Butyl-dimethylsilyl chloride (115 mg, 0.76 mmol) was added in one portion to a stirred solution of [rac]-1-[4-methyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-yl]-butane-1,4-diol (212 mg, 0.64 mmol) in pyridine (2 ml) at 0° C. The solution was naturally warmed to ambient temperature and stirred for 14 h. Pyridine was removed under reduced pressure and the residue dissolved in ethyl acetate. The solution was washed with 1 M aqueous HCl solution and two times with water and dried over sodium sulfate. The solvent was removed under reduced pressure and the residue was purified by column chromatography (silica gel, n-heptane/ethyl acetate) to give 120 mg (0.27 mmol, 42%) of the title compound as colorless crystals.

Workup

  1. customPyridine was removed under reduced pressure
  2. dissolutionthe residue dissolved in ethyl acetate
  3. washThe solution was washed with 1 M aqueous HCl solution and two times with water
  4. dry with materialdried over sodium sulfate
  5. customThe solvent was removed under reduced pressure
  6. customthe residue was purified by column chromatography (silica gel, n-heptane/ethyl acetate)

Sources & evidence

ORD record
ord-3db92b79260743a9a34af79838eaf603
Source dataset
uspto-grants-2007_06
Patent number
US07235572B2

Reaction notes

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