Ethyl Acetate → Tert-butyl (2-((4-iodobenzyl)amino)-2-oxoethyl)carbamate

HRID 2284792Notes

Reaction equation

HRID 2284792 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].Cl.[I:14][C:15]1[CH:22]=[CH:21][C:18]([CH2:19][NH2:20])=[CH:17][CH:16]=1.C(=O)([O-])O.[Na+].C(OCC)(=O)C>O1CCCC1.CN1CCOCC1.ClC(OCC(C)C)=O>[I:14][C:15]1[CH:22]=[CH:21][C:18]([CH2:19][NH:20][C:10](=[O:12])[CH2:9][NH:8][C:1](=[O:2])[O:3][C:4]([CH3:5])([CH3:6])[CH3:7])=[CH:17][CH:16]=1

Participants

8

Reactant 4

HCID 8857Ethyl AcetateHCID 78288N-(tert-butoxycarbonyl)glycineHCID 516892Sodium BicarbonateHCID 16217505(4-Iodophenyl)methanamine hydrochloride

Product 1

HCID 90052505Tert-butyl (2-((4-iodobenzyl)amino)-2-oxoethyl)carbamateYield 118.8%

Reagents, catalysts & solvents 3

HCID 79724-MethylmorpholineSolventHCID 8028TetrahydrofuranSolventHCID 62365Isobutyl chloroformateSolvent

Procedure

To a solution of N-Boc-glycine (325 mg) in tetrahydrofuran (3 mL), N-methylmorpholine (1.0 mL) and isobutyl chloroformate (244 μL) were added under ice cooling, and the mixture was stirred at the same temperature for 30 minutes. To the reaction mixture, 4-iodobenzylamine hydrochloride (250 mg) was added under ice cooling, and the mixture was stirred at the same temperature for 1 hour and 30 minutes. 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-iodobenzyl)amino)-2-oxoethyl)carbamate (R4, 430 mg).

Workup

  1. stirringthe mixture was stirred at the same temperature for 1 hour and 30 minutes
  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-a576e91110cf4bc78969bea3e83c59ae
Source dataset
uspto-grants-2015_09
Patent number
US09145415B2

Reaction notes

Loading…