Sulfuric Acid → HCID 86096911, compound

HRID 32825Notes

Reaction equation

HRID 32825 reaction equation
COC(=O)[CH:4]([O:13][CH3:14])[C:5]([C:7]1[N:8]=[C:9]([NH2:12])[S:10][CH:11]=1)=[O:6].[OH-].[Na+].S(=O)(=O)(O)O.C(=O)(O)[O-].[Na+]>O1CCCC1>[NH2:12][C:9]1[S:10][CH:11]=[C:7]([C:5](=[O:6])[CH2:4][O:13][CH3:14])[N:8]=1

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 516892Sodium BicarbonateHCID 86603388HCID 86603388, compound

Product 1

HCID 86096911HCID 86096911, compoundYield 42.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 3-(2-amino-thiazol-4-yl)-2-methoxy-3-oxo-propionic acid methyl ester (765 mg, 3.3 mmol) in tetrahydrofuran (25 ml) was added 1M aqueous sodium hydroxide (4.0 ml, 4.0 mmol) at room temperature. The mixture was stirred for 2 hours then cooled to 0° C. 1 N aqueous sulfuric acid (33 mL, 33.2 mmol) was added and the reaction was warmed to 40° C. for 30 minutes. The reaction mixture was then cooled to 0° C. and made basic with saturated aqueous sodium bicarbonate. The suspension was extracted with ethyl acetate, the combined organic extracts washed with water, brine and dried over magnesium sulfate. The crude product was purified by chromatography over silica gel eluted with 7:3 ethyl acetate/hexanes to give 1-(2-amino-thiazol-4-yl)-2-methoxy-ethanone as a yellow oil (240 mg, 42% yield).

Workup

  1. temperaturethe reaction was warmed to 40° C. for 30 minutes
  2. temperatureThe reaction mixture was then cooled to 0° C.
  3. extractionThe suspension was extracted with ethyl acetate
  4. washthe combined organic extracts washed with water, brine
  5. dry with materialdried over magnesium sulfate
  6. customThe crude product was purified by chromatography over silica gel
  7. washeluted with 7:3 ethyl acetate/hexanes

Sources & evidence

ORD record
ord-aa5adbbac7b6495990d705f3ab1bd549
Source dataset
uspto-grants-2008_09
Patent number
US07427635B2

Reaction notes

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