Dichloromethane → N-[5-((R)-2-amino-1-triethylsilyloxyethyl)-2-hydroxyphenyl]methanesulfonamide
Reaction equation
[N:1]([CH2:4][C@@H:5]([C:14]1[CH:15]=[CH:16][C:17]([O:25]CC2C=CC=CC=2)=[C:18]([NH:20][S:21]([CH3:24])(=[O:23])=[O:22])[CH:19]=1)[O:6][Si:7]([CH2:12][CH3:13])([CH2:10][CH3:11])[CH2:8][CH3:9])=[N+]=[N-].C(Cl)Cl>CO.[C].[Pd]>[NH2:1][CH2:4][C@@H:5]([C:14]1[CH:15]=[CH:16][C:17]([OH:25])=[C:18]([NH:20][S:21]([CH3:24])(=[O:22])=[O:23])[CH:19]=1)[O:6][Si:7]([CH2:10][CH3:11])([CH2:8][CH3:9])[CH2:12][CH3:13]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Procedure
A suspension of N-[5-((R)-2-azido-1-triethylsilyloxyethyl)-2-benzyloxyphenyl]methanesulfonamide (1.84 g) and 10% palladium-carbon (0.18 g) in methanol (15 mL) /methylene chloride (15 mL) was stirred at room temperature for 5 hrs under an atmosphere of hydrogen. The catalyst was removed by filtration, and the solvent was evaporated under reduced pressure to afford N-[5-((R)-2-amino-1-triethylsilyloxyethyl)-2-hydroxyphenyl]methanesulfonamide as a crude product. The crude N-[5-((R)-2-amino-1-triethylsilyloxyethyl)-2-hydroxyphenyl]methanesulfonamide was dissolved in tetrahydrofuran (40 mL), and 2,5-dioxopyrrolidin-1-yl (4-bromophenoxy)acetate (1.39 g) was added to the solution. After being stirred at room temperature for 3 hrs, the reaction mixture was concentrated in vacuo, and the residue was purified by medium-pressure silica gel column chromatography (eluent: n-hexane/ethyl acetate=1/1) to afford the title compound (1.01 g).
Workup
- customThe catalyst was removed by filtration
- customthe solvent was evaporated under reduced pressure
Sources & evidence
- ORD record
- ord-bf7d54d627e64dd989639f0c19388cb4
- Source dataset
- uspto-grants-2008_08
- Patent number
- US07417169B2
Reaction notes
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