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

HRID 349126Notes

Reaction equation

HRID 349126 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-5b9baca40e22447f82347853d0190519
Source dataset
uspto-grants-2007_02
Patent number
US07176242B2

Reaction notes

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