Toluene → HCID 59774430, compound

HRID 571610Notes

Reaction equation

HRID 571610 reaction equation
[C:1]([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])(=[O:4])[NH:2][NH2:3].[C:10]([O:14][CH2:15][CH3:16])(=[O:13])[CH:11]=O.C1(C)C=CC=CC=1.C(OCC)(=O)C>C1COCC1>[C:6]([O:5][C:1]([NH:2]/[N:3]=[CH:11]/[C:10]([O:14][CH2:15][CH3:16])=[O:13])=[O:4])([CH3:9])([CH3:8])[CH3:7]

Participants

6

Reactant 4

HCID 1140TolueneHCID 8857Ethyl AcetateHCID 70091tert-Butyl carbazateHCID 70211Ethyl oxoacetate

Product 1

HCID 59774430HCID 59774430, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of t-butyl carbazate (25.5 g, 193 mmol) in THF (60 ml) was added 47% ethyl glyoxylate in toluene (polymer type) (46.1 g, 212 mmol), and stirred at 60° C. for minutes. The reaction solution was cooled to room temperature, and concentrated under reduced pressure. The resulting solid was washed with a mixed solvent of hexane:ethyl acetate=5:1 to give 33.9 g of Compound (X-1) (yield: 80%) as colorless solid.

Workup

  1. temperatureThe reaction solution was cooled to room temperature
  2. concentrationconcentrated under reduced pressure
  3. washThe resulting solid was washed with a mixed solvent of hexane

Sources & evidence

ORD record
ord-6e910cc5b0624a109990934b08e44558
Source dataset
uspto-grants-2015_05
Patent number
US09029295B2

Reaction notes

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