tert-Butyl carbazate → HCID 67336794, compound

HRID 451570Notes

Reaction equation

HRID 451570 reaction equation
[CH3:1][O:2][C:3](=[O:15])[CH:4]([O:11][CH2:12][CH:13]=O)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[C:16]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])(=[O:19])[NH:17][NH2:18]>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3](=[O:15])[CH:4]([C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1)[O:11][CH2:12][CH:13]=[N:18][NH:17][C:16]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19]

Participants

4

Reactant 2

HCID 70091tert-Butyl carbazateHCID 86656221HCID 86656221, compound

Product 1

HCID 67336794HCID 67336794, compoundYield 67.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
65 °C

Procedure

(2-Oxo-ethoxy)-phenyl-acetic acid methyl ester (2.7 g, 13.0 mmol) and tert-butyl carbazate (1.75 g, 13.0 mmol) were dissolved in toluene (290 mL) and heated to 65° C. over night. The reaction mixture was concentrated in vacuo and the residue was purified by flash chromatography (silica gel, 100 g, 0% to 100% EtOAc in heptane over 60 minutes) to give the title compound as yellow viscous oil (2.81 g, 67%).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customthe residue was purified by flash chromatography (silica gel, 100 g, 0% to 100% EtOAc in heptane over 60 minutes)

Sources & evidence

ORD record
ord-2cf07699e35746a7a32a7d3f704d60be
Source dataset
uspto-grants-2013_07
Patent number
US08486967B2

Reaction notes

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