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

HRID 557848Notes

Reaction equation

HRID 557848 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 framed 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. filtrationThe precipitate framed was filtered
  4. washwashed with water

Sources & evidence

ORD record
ord-de0daedfbb13434e840aa1ba19683ca6
Source dataset
uspto-grants-2011_11
Patent number
US08058288B2

Reaction notes

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