Water → (1R,2R)-2-(4-Fluoro-phenyl)-cyclopropanecarboxylic acid
Reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:10][CH:9]2[C:11](N2C3CC4C(C)(C)C3(CC4)CS2(=O)=O)=[O:12])=[CH:4][CH:3]=1.[OH2:27].[OH-].[Li+].O>O1CCCC1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C@@H:8]2[CH2:10][C@H:9]2[C:11]([OH:12])=[O:27])=[CH:6][CH:7]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 50 °C
Procedure
A suspension of the product from step b) (3.74 g) and lithium hydroxide monohydrate (4.11 g) in tetrahydrofuran (100 ml)/water (3 ml) was stirred at 50° C. for 24 hours. The reaction mixture was concentrated in vacuo, and the residue dissolved in water (100 ml), acidified with 2N HCl and extracted into dichloromethane (3×75 ml). The organics were dried and concentrated. Purification (SiO2, isohexane:diethylether 2:1 as eluant) gave the subtitle compound as a colourless solid (1.78 g).
Workup
- concentrationThe reaction mixture was concentrated in vacuo
- dissolutionthe residue dissolved in water (100 ml)
- extractionextracted into dichloromethane (3×75 ml)
- customThe organics were dried
- concentrationconcentrated
- customPurification (SiO2, isohexane:diethylether 2:1 as eluant)
Sources & evidence
- ORD record
- ord-2563ffb8d4104b358c2630e5b06c32c4
- Source dataset
- uspto-grants-2007_07
- Patent number
- US07250419B2
Reaction notes
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