Ethyl Acetate → Methyl 4-(((benzyloxycarbonyl)(methyl)amino)methyl)benzoate

HRID 415174Notes

Reaction equation

HRID 415174 reaction equation
[CH3:1][NH:2][CH2:3][C:4]1[CH:13]=[CH:12][C:7]([C:8]([O:10][CH3:11])=[O:9])=[CH:6][CH:5]=1.[C:14](Cl)(=[O:23])[O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C(=O)(O)[O-].[Na+].C(OCC)(=O)C>C1COCC1.O>[CH2:16]([O:15][C:14]([N:2]([CH2:3][C:4]1[CH:13]=[CH:12][C:7]([C:8]([O:10][CH3:11])=[O:9])=[CH:6][CH:5]=1)[CH3:1])=[O:23])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 10387Benzyl chloroformateHCID 516892Sodium BicarbonateHCID 11194668Methyl 4-[(methylamino)methyl]benzoate

Product 1

HCID 66621459Methyl 4-(((benzyloxycarbonyl)(methyl)amino)methyl)benzoateYield 53.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Methyl 4-((methylamino)methyl)benzoate was dissolved in the mixed solution of THF (12 mL) and water (12 mL), then benzyl carbonochloridate (2.57 g, 15.0 mmol) was dropped into it. To the mixture sodium bicarbonate (1.7 g, 20.5 mmol) was added and the mixture was stirred at room temperature overnight. The mixture was poured into ethyl acetate (50 mL×3) and the organic layer was washed with saturated sodium bicarbonate solution, dried with anhydrous sodium sulfate and condensed to get methyl 4-(((benzyloxycarbonyl)(methyl)amino)methyl)benzoate (2.3 g, 53.5%), LC-MS (ESI) m/z 314 [M+1]+.

Workup

  1. washthe organic layer was washed with saturated sodium bicarbonate solution
  2. dry with materialdried with anhydrous sodium sulfate and condensed

Sources & evidence

ORD record
ord-c9fb1985447b494fa67939d1be3e1ff2
Source dataset
uspto-grants-2012_01
Patent number
US08088760B2

Reaction notes

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