Ethyl bromoacetate → [Tert-butoxycarbonyl-[2-(5,6,7,8-tetrahydro-[1,8]naphthyridin-2-yl)-ethyl]-amino]-acetic acid ethyl ester
Reaction equation
Cl.Cl.[N:3]1[C:12]2[NH:11][CH2:10][CH2:9][CH2:8][C:7]=2[CH:6]=[CH:5][C:4]=1[CH2:13][CH2:14][NH2:15].C(N(CC)C(C)C)(C)C.Br[CH2:26][C:27]([O:29][CH2:30][CH3:31])=[O:28].[O:32](C(OC(C)(C)C)=O)[C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=O>C(#N)C.C(OCC)(=O)C>[CH2:30]([O:29][C:27](=[O:28])[CH2:26][N:15]([C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:32])[CH2:14][CH2:13][C:4]1[CH:5]=[CH:6][C:7]2[CH2:8][CH2:9][CH2:10][NH:11][C:12]=2[N:3]=1)[CH3:31]Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 50 °C
Procedure
To a solution of 10-7 (2.0 g, 7.8 mmol) and N,N-diisopropylethylamine (6.8 mL) in acetonitrile (50 mL) at 0° C. was added ethyl bromoacetate (0.975 mL, 8.6 mmol). The mixture was stirred at 50° C. for 15 h, then cooled to 25° C. and BOC2O (1.7 g, 7.8 mmol) was added. After 1 h, the mixture was diluted with ethyl acetate, washed with sat. NaHCO3, brine, dried (MgSO4) and concentrated. Flash chromatography (silica, 50-60% EtOAc/hexanes) gave 10-8 as a colorless oil.
Workup
- temperaturecooled to 25° C.
- waitAfter 1 h
- washwashed with sat. NaHCO3, brine
- dry with materialdried (MgSO4)
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-887a6c41a80641fba41396dda8ed3aa4
- Source dataset
- uspto-grants-2001_10
- Patent number
- US06297249B1
Reaction notes
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