Lithium Hydroxide → 2-(3-Hydroxybutan-2-ylamino)thiazole-4-carboxylic acid

HRID 872659Notes

Reaction equation

HRID 872659 reaction equation
[OH:1][CH:2]([CH3:15])[CH:3]([NH:5][C:6]1[S:7][CH:8]=[C:9]([C:11]([O:13]C)=[O:12])[N:10]=1)[CH3:4].[OH-].[Li+]>C1COCC1.O>[OH:1][CH:2]([CH3:15])[CH:3]([NH:5][C:6]1[S:7][CH:8]=[C:9]([C:11]([OH:13])=[O:12])[N:10]=1)[CH3:4]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 87294675Methyl 2-(3-hydroxybutan-2-ylamino)thiazole-4-carboxylate

Product 1

HCID 866702512-(3-Hydroxybutan-2-ylamino)thiazole-4-carboxylic acid

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

Methyl 2-(3-hydroxybutan-2-ylamino)thiazole-4-carboxylate (1.092 g, 4.75 mmol) was dissolved in THF/water (9:1) mixture and 1M lithium hydroxide (9.49 ml, 9.49 mmol) was added slowly. The reaction mixture was stirred at RT for 1 h and evaporated to dryness. DCM and water was added and pH was adjusted to 2. Acidic water phase was washed twice with DCM and evaporated to dryness. Evaporation residue was dissolved in ethanol, a precipitation was filtered and the filtrate was evaporated to dryness to give a crude product. m/z [216.3+1].

Workup

  1. additionwas added slowly
  2. customevaporated to dryness
  3. additionDCM and water was added
  4. washAcidic water phase was washed twice with DCM
  5. customevaporated to dryness
  6. customEvaporation residue
  7. dissolutionwas dissolved in ethanol
  8. customa precipitation
  9. filtrationwas filtered
  10. customthe filtrate was evaporated to dryness

Sources & evidence

ORD record
ord-5ca7acb4135b4aa79f642a01fb27cae0
Source dataset
uspto-grants-2015_03
Patent number
US08975254B2

Reaction notes

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