Acetic Acid → HCID 67548868, compound

HRID 43510Notes

Reaction equation

HRID 43510 reaction equation
[C:1]([O:5][C:6]([N:8]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[C:9]1[S:10][C:11]([C:23]([O:25][CH2:26][CH3:27])=[O:24])=[C:12]([CH2:14][O:15][Si](C(C)(C)C)(C)C)[N:13]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CCCC[N+](CCCC)(CCCC)CCCC.[F-].C(O)(=O)C.C(OCC)(=O)C>C1COCC1>[C:1]([O:5][C:6]([N:8]([C:28]([O:30][C:31]([CH3:32])([CH3:34])[CH3:33])=[O:29])[C:9]1[S:10][C:11]([C:23]([O:25][CH2:26][CH3:27])=[O:24])=[C:12]([CH2:14][OH:15])[N:13]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 8857Ethyl AcetateHCID 2724141Tetrabutylammonium FluorideHCID 68405814Ethyl 2-[bis(tert-butoxycarbonyl)amino]-4-({[tert-butyl(dimethyl)silyl]oxy}methyl)-1,3-thiazole-5-carboxylate

Product 1

HCID 67548868HCID 67548868, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Ethyl 2-[bis(tert-butoxycarbonyl)amino]-4-({[tert-butyl(dimethyl)silyl]oxy}methyl)-1,3-thiazole-5-carboxylate obtained in Example (62b) (2.87 g, 5.55 mmol) was dissolved in THF (60 mL). TBAF (1 M solution in THF, 9.3 mL) and acetic acid (0.48 mL, 8.39 mmol) were added, followed by stirring for 15 hours. Ethyl acetate was added to the reaction solution, and the organic layer was washed with saturated aqueous sodium bicarbonate solution and brine, and dried over anhydrous sodium sulfate. Following concentration under reduced pressure, the residue was purified by silica gel column chromatography (elution solvent: hexane/ethyl acetate=90/10, 70/30) to obtain 1.83 g of the title compound as a white solid (82%).

Workup

  1. washthe organic layer was washed with saturated aqueous sodium bicarbonate solution and brine
  2. dry with materialdried over anhydrous sodium sulfate
  3. concentrationconcentration under reduced pressure
  4. customthe residue was purified by silica gel column chromatography (elution solvent: hexane/ethyl acetate=90/10, 70/30)

Sources & evidence

ORD record
ord-e903687a207c495d9c21fe0767f660aa
Source dataset
uspto-grants-2013_09
Patent number
US08536197B2

Reaction notes

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