Trifluoroacetic acid → N-[2-amino-2-(4-chlorophenyl)ethyl]methanesulfonamide
Reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([NH:15]C(=O)OC(C)(C)C)[CH2:9][NH:10][S:11]([CH3:14])(=[O:13])=[O:12])=[CH:4][CH:3]=1.FC(F)(F)C(O)=O>>[NH2:15][CH:8]([C:5]1[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=1)[CH2:9][NH:10][S:11]([CH3:14])(=[O:13])=[O:12]Participants
3
Procedure
tert-butyl 1-(4-chlorophenyl)-2-(methylsulfonamido)ethylcarbamate (Intermediate 74) (151 mg, 0.43 mmol) was treated with trifluoroacetic acid (2 mL). The solution was stirred for 1 hour at room temperature. The mixture was concentrated under reduced pressure. The crude product was purified by ion exchange chromatography, using an SCX column. The residue was loaded onto the column in methanol and washed with methanol. The desired product was eluted from the column using 2M ammonia in methanol and pure fractions were evaporated to dryness to afford N-(2-amino-2-(4-chlorophenyl)ethyl)methanesulfonamide (93 mg, 86%) as a colourless crystalline solid.
Workup
- concentrationThe mixture was concentrated under reduced pressure
- customThe crude product was purified by ion exchange chromatography
- washwashed with methanol
- washThe desired product was eluted from the column
- customwere evaporated to dryness
Sources & evidence
- ORD record
- ord-4a343d4eac324685964448e2906487cd
- Source dataset
- uspto-grants-2012_01
- Patent number
- US08101623B2
Reaction notes
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