Tetrahydrofuran → Methyl 4-amino-1,3-thiazole-5-carboxylate

HRID 1161515Notes

Reaction equation

HRID 1161515 reaction equation
[CH3:1][O:2][C:3]([C:5]1[S:9][C:8](S(C)(=O)=O)=[N:7][C:6]=1[NH2:14])=[O:4].C1COCC1.[BH4-].[Na+].C(OCC)(=O)C>CO.O>[CH3:1][O:2][C:3]([C:5]1[S:9][CH:8]=[N:7][C:6]=1[NH2:14])=[O:4]

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 8857Ethyl AcetateHCID 4311764Sodium borohydrideHCID 59511825Methyl 4-amino-2-(methylsulfonyl)thiazole-5-carboxylate

Product 1

HCID 15832487Methyl 4-amino-1,3-thiazole-5-carboxylateYield 60.8%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of 37.6 g of 4-amino-2-methanesulfonylthiazole-5-carboxylic acid methyl ester in 1 liter of a methanol:THF=1:1 mixed solvent at room temperature there was added 15 g of sodium borohydride in small portions over a period of 10 hours. The reaction mixture was stirred at room temperature for 40 hours, and then poured into a mixture of 6 liters of ethyl acetate and 3 liters of water. The organic layer was washed with 3 liters of water and 3 liters of saturated brine, and the aqueous layer was extracted again with ethyl acetate. The organic layers were combined and dried over anhydrous magnesium sulfate. The desiccating agent was filtered off and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate-heptane) to give the title compound (15.3 g) as a light yellow solid.

Workup

  1. washThe organic layer was washed with 3 liters of water and 3 liters of saturated brine
  2. extractionthe aqueous layer was extracted again with ethyl acetate
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationThe desiccating agent was filtered off
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (ethyl acetate-heptane)

Sources & evidence

ORD record
ord-ee8e1f810e1f48c6a9f8a95865efe22c
Source dataset
uspto-grants-2010_10
Patent number
US07816522B2

Reaction notes

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