Ethyl Acetate → HCID 23655191, compound

HRID 415330Notes

Reaction equation

HRID 415330 reaction equation
[Cl-].[CH3:2][O:3][C:4]([C:6]1[CH:11]=[CH:10][C:9]([CH2:12][CH2:13][NH3+:14])=[CH:8][CH:7]=1)=[O:5].Cl[C:16]([O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:17].C(=O)(O)[O-].[Na+].C(OCC)(=O)C>O1CCCC1.O>[CH2:19]([O:18][C:16]([NH:14][CH2:13][CH2:12][C:9]1[CH:10]=[CH:11][C:6]([C:4]([O:3][CH3:2])=[O:5])=[CH:7][CH:8]=1)=[O:17])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 10387Benzyl chloroformateHCID 516892Sodium BicarbonateHCID 11183520HCID 11183520, compound

Product 1

HCID 23655191HCID 23655191, compoundYield 77%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

2-(4-(Methoxycarbonyl)phenyl)ethanaminium chloride (3 g, 13.9 mmol) was dissolved in the mixed solution of tetrahydrofuran (30 mL) and water (30 mL), and then benzyl chloroformate (2.37 g, 13.9 mmol) was dropped into it. To the mixture, sodium bicarbonate (2.9 g, 34.7 mmol) was added and the mixture was stirred at room temperature for 1.5 h. Then 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-(2-(benzyloxycarbonylamino)ethyl)benzoate (3.3 g, yield 77%). 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-28f833abb4674cf1b9ceaec7c658c95b
Source dataset
uspto-grants-2012_01
Patent number
US08088760B2

Reaction notes

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