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

HRID 969110Notes

Reaction equation

HRID 969110 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 reation mixture was concentrated and the residue was adjusted to be acidic (pH=˜3) by 1N HCl aqueous solution. The precipitate fromed 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 reation mixture was concentrated
  3. filtrationThe precipitate fromed was filtered
  4. washwashed with water

Sources & evidence

ORD record
ord-c07dfd75f94f45679d96699219f54f68
Source dataset
uspto-grants-2007_12
Patent number
US07304081B2

Reaction notes

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