Water → Methyl 3-(2-(((tert-butoxy)carbonyl)amino)ethyl)benzoate
Reaction equation
[NH2:1][CH2:2][CH2:3][C:4]1[CH:5]=[C:6]([CH:11]=[CH:12][CH:13]=1)[C:7]([O:9][CH3:10])=[O:8].[O:14](C(OC(C)(C)C)=O)[C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=O.O>O1CCCC1>[C:18]([O:17][C:15]([NH:1][CH2:2][CH2:3][C:4]1[CH:5]=[C:6]([CH:11]=[CH:12][CH:13]=1)[C:7]([O:9][CH3:10])=[O:8])=[O:14])([CH3:21])([CH3:20])[CH3:19]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 22 °C
Procedure
To 5.12 g (28.6 mmol) of methyl 3-(2-aminoethyl)benzoate in 71 mL tetrahydrofuran (THF) was added 7.48 g (34.3 mmol) of BOC2O. The mixture was stirred for about 16 h at 22° C. and 100 mL of water was added. The mixture was extracted with ethyl acetate (2×100 mL) and the organic phase was washed with brine, dried (Na2SO4) and evaporated. The residue was purified by flash chromatography on silica gel, eluting first with hexane and then gradually increasing to 20% ethyl acetate/hexane to give methyl 3-(2-(tert-butoxycarbonylamino)ethyl)benzoate which was further converted to 2d in a manner analogous to Method B.
Workup
- extractionThe mixture was extracted with ethyl acetate (2×100 mL)
- washthe organic phase was washed with brine
- dry with materialdried (Na2SO4)
- customevaporated
- customThe residue was purified by flash chromatography on silica gel
- washeluting first with hexane
- temperaturegradually increasing to 20% ethyl acetate/hexane
Sources & evidence
- ORD record
- ord-3f9a0ebadb354409ba2a3b4b9b3c09b0
- Source dataset
- uspto-grants-2016_01
- Patent number
- US09227918B2
Reaction notes
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