Ethyl Acetate → HCID 90051708, compound

HRID 2284791Notes

Reaction equation

HRID 2284791 reaction equation
[C:1]([NH:8][CH2:9][C:10]([OH:12])=O)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[Br:13][C:14]1[CH:15]=[C:16]([CH:20]=[CH:21][CH:22]=1)[CH2:17][CH2:18][NH2:19].C(=O)([O-])O.[Na+].C(OCC)(=O)C>O1CCCC1.CN1CCOCC1.ClC(OCC(C)C)=O>[Br:13][C:14]1[CH:15]=[C:16]([CH:20]=[CH:21][CH:22]=1)[CH2:17][CH2:18][NH:19][C:10](=[O:12])[CH2:9][NH:8][C:1](=[O:2])[O:3][C:4]([CH3:5])([CH3:6])[CH3:7]

Participants

8

Reactant 4

HCID 8857Ethyl AcetateHCID 78288N-(tert-butoxycarbonyl)glycineHCID 516892Sodium BicarbonateHCID 70217363-Bromophenethylamine

Product 1

HCID 90051708HCID 90051708, compound

Reagents, catalysts & solvents 3

HCID 79724-MethylmorpholineSolventHCID 8028TetrahydrofuranSolventHCID 62365Isobutyl chloroformateSolvent

Procedure

To a solution of N-Boc-glycine (175 mg) in tetrahydrofuran (1 mL), N-methylmorpholine (165 μL) and isobutyl chloroformate (131 μL) were added under ice cooling, and the mixture was stirred at the same temperature for 40 minutes. To the reaction mixture, 3-bromophenethylamine (100 μL) was added under ice cooling, and the mixture was stirred at room temperature for 5 hours. To the reaction mixture, saturated aqueous sodium hydrogencarbonate and ethyl acetate were added. The organic layer was separated, and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to obtain tert-butyl (2-((3-bromophenethyl)amino)-2-oxoethyl)carbamate (R1, 290 mg).

Workup

  1. stirringthe mixture was stirred at room temperature for 5 hours
  2. customThe organic layer was separated
  3. dry with materialdried over anhydrous sodium sulfate
  4. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-8ee7344871c7495fa66af6187d3cf6bc
Source dataset
uspto-grants-2015_09
Patent number
US09145415B2

Reaction notes

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