Water → Ethyl 2-((tert-butoxycarbonyl)amino)-1,3-thiazole-4-carboxylate

HRID 1714726Notes

Reaction equation

HRID 1714726 reaction equation
[C:1]([O:8]C([O-])=O)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=O.[NH2:12][C:13]1[S:14][CH:15]=[C:16]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[N:17]=1.C(N(CC)CC)C.O>CN(C1C=CN=CC=1)C.C1COCC1>[C:4]([O:3][C:1]([NH:12][C:13]1[S:14][CH:15]=[C:16]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[N:17]=1)=[O:8])([CH3:5])([CH3:6])[CH3:7]

Participants

7

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 73216Ethyl 2-aminothiazole-4-carboxylateHCID 22064466Tert-butyldicarbonate

Product 1

HCID 22280595Ethyl 2-((tert-butoxycarbonyl)amino)-1,3-thiazole-4-carboxylateYield 94.9%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolvent

Procedure

1.39 g of tert-butyl dicarbonate was added to a solution in which 1.00 g of ethyl 2-amino-1,3-thiazole-4-carboxylate, 0.88 g of triethylamine, and 0.07 g of DMAP were dissolved in THF, under ice cooling. Then, after the reaction mixture was stirred at room temperature for 1 hr, it was poured into water and extracted with ethyl acetate. The organic layer was washed with an aqueous 2N-hydrochloric acid solution and dried over anhydrous magnesium sulfate. After distilling off the solvent, the obtained crude product was washed with a mixed solvent of hexane and t-butyl methyl ether to obtain 1.5 g of the aimed ethyl 2-(tert-butoxycarbonyl)amino-1,3-thiazole-4-carboxylate.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with an aqueous 2N-hydrochloric acid solution
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationAfter distilling off the solvent
  5. customthe obtained crude product
  6. washwas washed with a mixed solvent of hexane and t-butyl methyl ether

Sources & evidence

ORD record
ord-f4d7104bb08846949c12a60010d19e47
Source dataset
uspto-grants-2010_09
Patent number
US07799738B2

Reaction notes

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