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

HRID 2275566Notes

Reaction equation

HRID 2275566 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 fumed 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 fumed was filtered
  4. washwashed with water

Sources & evidence

ORD record
ord-82be7dde127f4434b5cc984b2e18e023
Source dataset
uspto-grants-2015_09
Patent number
US09126927B2

Reaction notes

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