Water → 2,2,2-Trichloroethyl 5-tert-butyl-3-(hydroxymethyl)-2-methoxyphenylcarbamate
Reaction equation
[NH2:1][C:2]1[C:3]([O:14][CH3:15])=[C:4]([CH2:12][OH:13])[CH:5]=[C:6]([C:8]([CH3:11])([CH3:10])[CH3:9])[CH:7]=1.C(N(CC)C(C)C)(C)C.Cl[C:26]([O:28][CH2:29][C:30]([Cl:33])([Cl:32])[Cl:31])=[O:27].O>C1COCC1>[C:8]([C:6]1[CH:5]=[C:4]([CH2:12][OH:13])[C:3]([O:14][CH3:15])=[C:2]([NH:1][C:26](=[O:27])[O:28][CH2:29][C:30]([Cl:33])([Cl:32])[Cl:31])[CH:7]=1)([CH3:11])([CH3:9])[CH3:10]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of (3-amino-5-tert-butyl-2-methoxyphenyl)methanol (1.72 g, 8.23 mmol) and N,N-diisopropylethylamine (2.15 mL, 12.3 mmol) in THF (27.4 mL) was cooled to 0° C., and 2,2,2-trichloroethyl chloroformate (1.24 mL, 9.01 mmol) was added, followed by stirring the mixture for 10 minutes. Water was added to the reaction solution and the aqueous layer was extracted with ethyl acetate and then the organic layer was washed with saturated brine. The organic layer was dried over anhydrous sodium sulfate and filtered, and then the solvent was evaporated under reduced pressure. The obtained residue was purified by column chromatography (silica gel, hexane/ethyl acetate=75/25-50/50) to obtain 2.23 g of the captioned compound (71% yield).
Workup
- extractionthe aqueous layer was extracted with ethyl acetate
- washthe organic layer was washed with saturated brine
- dry with materialThe organic layer was dried over anhydrous sodium sulfate
- filtrationfiltered
- customthe solvent was evaporated under reduced pressure
- customThe obtained residue was purified by column chromatography (silica gel, hexane/ethyl acetate=75/25-50/50)
Sources & evidence
- ORD record
- ord-1b36a8f1fb61491593b5af8626af9c2b
- Source dataset
- uspto-grants-2014_02
- Patent number
- US08653304B2
Reaction notes
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