Lithium hydroxide, monohydrate → [4-(2-Amino-1,3-thiazol-4-yl)phenyl]cyclopropanecarboxylic acid

HRID 504310Notes

Reaction equation

HRID 504310 reaction equation
O.[OH-].[Li+].[NH2:4][C:5]1[S:6][CH:7]=[C:8]([C:10]2[CH:15]=[CH:14][C:13]([C:16]3([C:19]([O:21]C)=[O:20])[CH2:18][CH2:17]3)=[CH:12][CH:11]=2)[N:9]=1>C1COCC1.O>[NH2:4][C:5]1[S:6][CH:7]=[C:8]([C:10]2[CH:11]=[CH:12][C:13]([C:16]3([C:19]([OH:21])=[O:20])[CH2:18][CH2:17]3)=[CH:14][CH:15]=2)[N:9]=1

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 86602276Methyl1-[4-(2-amino-1,3-thiazol-4-yl)phenyl]cyclopropanecarboxylate

Product 1

HCID 86602277[4-(2-Amino-1,3-thiazol-4-yl)phenyl]cyclopropanecarboxylic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Lithium hydroxide monohydrate (0.24 g, 5.8 mmol) was added to a mixture of methyl 1-[4-(2-amino-1,3-thiazol-4-yl)phenyl]cyclopropanecarboxylate (0.2 g, 0.73 mmol) in THF (3.0 ml) and water (1.0 mL), and the resulting mixture was refluxed for 30 minutes. Then the reaction mixture was concentrated and the residue was adjusted to be acidic (pH==3) by 1N HCl aqueous solution. The precipitate formed was filtered and washed with water to afford the desired product. LC-MS: 261.0 (M+H)+.

Workup

  1. temperaturethe resulting mixture was refluxed for 30 minutes
  2. concentrationThen the reaction mixture was concentrated
  3. customThe precipitate formed
  4. filtrationwas filtered
  5. washwashed with water

Sources & evidence

ORD record
ord-31c70c56da8f45ce832358552d08fe53
Source dataset
uspto-grants-2010_08
Patent number
US07776874B2

Reaction notes

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