1,4-Dioxane → 2-Amino-1,3-thiazole-4-carboxylic acid, N-BOC protected

HRID 1714727Notes

Reaction equation

HRID 1714727 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1[S:10][CH:11]=[C:12]([C:14]([O:16]CC)=[O:15])[N:13]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].O.[OH-].[Li+].O1CCOCC1>O>[C:1]([O:5][C:6]([NH:8][C:9]1[S:10][CH:11]=[C:12]([C:14]([OH:16])=[O:15])[N:13]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 312751,4-DioxaneHCID 168937Lithium hydroxide, monohydrateHCID 22280595Ethyl 2-((tert-butoxycarbonyl)amino)-1,3-thiazole-4-carboxylate

Product 1

HCID 15020512-Amino-1,3-thiazole-4-carboxylic acid, N-BOC protectedYield 91.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A mixture of 1.00 g of ethyl 2-(tert-butoxycarbonyl)amino-1,3-thiazole-4-carboxylate, 0.46 g of lithium hydroxide monohydrate, 10 mL of water and 10 mL of 1,4-dioxane was stirred at room temperature for 6 hrs. After the reaction mixture was diluted with water, it was washed with ethyl acetate. The separated aqueous phase was acidified with an aqueous 2N-hydrochloric acid solution and the precipitated crude product was washed with water and dried to obtain 0.82 g of the aimed 2-(tert-butoxycarbonyl)amino-1,3-thiazole-4-carboxylic acid.

Workup

  1. washwas washed with ethyl acetate
  2. customthe precipitated crude product
  3. washwas washed with water
  4. customdried

Sources & evidence

ORD record
ord-27eeb09cc7bd4f5f9156bb6ccab176a0
Source dataset
uspto-grants-2010_09
Patent number
US07799738B2

Reaction notes

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