Ethyl Acetate → HCID 90052494, compound

HRID 2284793Notes

Reaction equation

HRID 2284793 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:19]=[CH:18][C:17]([CH2:20][CH2:21][NH2:22])=[CH:16][CH:15]=1.C(=O)([O-])O.[Na+].C(OCC)(=O)C>O1CCCC1.CN1CCOCC1.ClC(OCC(C)C)=O>[Br:13][C:14]1[CH:19]=[CH:18][C:17]([CH2:20][CH2:21][NH:22][C:10](=[O:12])[CH2:9][NH:8][C:1](=[O:2])[O:3][C:4]([CH3:5])([CH3:6])[CH3:7])=[CH:16][CH:15]=1

Participants

8

Reactant 4

HCID 8857Ethyl AcetateHCID 78288N-(tert-butoxycarbonyl)glycineHCID 516892Sodium BicarbonateHCID 533915p-Bromophenethylamine

Product 1

HCID 90052494HCID 90052494, compound

Reagents, catalysts & solvents 3

HCID 79724-MethylmorpholineSolventHCID 8028TetrahydrofuranSolventHCID 62365Isobutyl chloroformateSolvent

Procedure

To a solution of N-Boc-glycine (175 mg) in tetrahydrofuran (2 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, 2-(4-bromophenyl)ethylamine (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-((4-bromophenethyl)amino)-2-oxoethyl)carbamate (R5).

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-15caded174094605af889ed8a7e7a21a
Source dataset
uspto-grants-2015_09
Patent number
US09145415B2

Reaction notes

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