Hydrochloric Acid → methyl N-{2-fluoro-4-chloro-5-(3-methylcyclopentyl)oxyphenyl}carbamate
Reaction equation
[F:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([O:9][C:10](OCC(C)C)=O)=[CH:4][C:3]=1[NH:17][C:18](=[O:21])[O:19][CH3:20].[C:22]1([CH3:38])[CH:27]=CC(S(OC2CCC(C)C2)(=O)=O)=[CH:24][CH:23]=1.C(=O)([O-])[O-].[K+].[K+].Cl>CO>[F:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([O:9][CH:10]2[CH2:24][CH2:23][CH:22]([CH3:38])[CH2:27]2)=[CH:4][C:3]=1[NH:17][C:18](=[O:21])[O:19][CH3:20]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of methyl N-(2-fluoro-4-chloro-5-isobutyloxycarbonyloxyphenyl)carbamate (5.37 g, 16.8 mmol) prepared by the process as shown in Reference Example 3, 3-methylcyclopentyl p-toluenesulfonate (5.0 g, 20.2 mmol) and potassium carbonate (2.32 g, 16.8 mmol) in methanol (50 ml) was stirred for 5 hours under refluxing. After completion of the reaction, the reaction mixture was poured into 1N hydrochloric acid (100 ml), and the mixture was extracted with ethyl acetate (50 ml×3 times). The organic layer was dried, and the solvent was distilled off under reduced pressure to obtain methyl N-{2-fluoro-4-chloro-5-(3-methylcyclopentyl)oxyphenyl}carbamate as grey white crystals (3.81 g, 12.6 mmol, 75.2% yield).
Workup
- temperatureunder refluxing
- customAfter completion of the reaction
- extractionthe mixture was extracted with ethyl acetate (50 ml×3 times)
- customThe organic layer was dried
- distillationthe solvent was distilled off under reduced pressure
Sources & evidence
- ORD record
- ord-4711a0e538724b95a76f5acf29fea76d
- Source dataset
- uspto-grants-1995_11
- Patent number
- US05464811
Reaction notes
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