Hydrochloric Acid → 2-[Methyl(methylsulfonyl)amino]-1,3-oxazole-4-carboxylic acid

HRID 14337Notes

Reaction equation

HRID 14337 reaction equation
[CH3:1][N:2]([S:13]([CH3:16])(=[O:15])=[O:14])[C:3]1[O:4][CH:5]=[C:6]([C:8]([O:10]CC)=[O:9])[N:7]=1.[OH-].[Li+].O1CCCC1.Cl>O>[CH3:1][N:2]([S:13]([CH3:16])(=[O:15])=[O:14])[C:3]1[O:4][CH:5]=[C:6]([C:8]([OH:10])=[O:9])[N:7]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 21086092Ethyl 2-[methyl(methylsulfonyl)amino]-1,3-oxazole-4-carboxylate

Product 1

HCID 210854712-[Methyl(methylsulfonyl)amino]-1,3-oxazole-4-carboxylic acidYield 82.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a 50 ml round bottom flask was added (61 mg, 0.2457 mmoles) ethyl 2-[methyl(methylsulfonyl)amino]-1,3-oxazole-4-carboxylate, (51.5 mg, 1.2274 mmoles, 5.0 eq.) lithium hydroxide, (2.5 ml) tetrahydrofuran and (1.5 ml) water. The reaction was agitated at ambient temperature for ˜2 hours. The reaction was complete by electrospray mass spec. The reaction was worked up by adding (5 ml) 1N HCl and then extracting with ethyl acetate. The organic layer was washed with water and brine and then dried with magnesium sulfate. The solution was then evaporated to dryness, leaving (44.6 mg) of 2-[methyl(methylsulfonyl)amino]-1,3-oxazole-4-carboxylic acid.

Workup

  1. extractionextracting with ethyl acetate
  2. washThe organic layer was washed with water and brine
  3. dry with materialdried with magnesium sulfate
  4. customThe solution was then evaporated to dryness

Sources & evidence

ORD record
ord-eb200b5b9a7246ccbd53a3d7b0c0fb9a
Source dataset
uspto-grants-2010_06
Patent number
US07727997B2

Reaction notes

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