Ethyl Acetate → HCID 131736175, compound

HRID 1052506Notes

Reaction equation

HRID 1052506 reaction equation
[Br:1][C:2]1[CH:6]=[CH:5][N:4]([NH:7][C:8](=O)[CH2:9]NC(=O)OCC2C=CC=CC=2)[C:3]=1[C:22](=[O:30])[NH:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.[C:31]1([CH3:41])[CH:36]=[CH:35][C:34](S([O-])(=O)=O)=[CH:33][CH:32]=1.[NH+:42]1C=CC=C[CH:43]=1.[C:48]([O:51]CC)(=[O:50])C>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:6]=[CH:5][N:4]2[C:3]=1[C:22](=[O:30])[N:23]([C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1)[C:8]([CH2:9][CH2:43][NH:42][C:48](=[O:50])[O:51][CH2:41][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)=[N:7]2

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 131736174HCID 131736174, compound

Product 1

HCID 131736175HCID 131736175, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of benzyl (2-((3-bromo-2-(phenylcarbamoyl)-1H-pyrrol-1-yl)amino)-2-oxoethyl)carbamate (7.81 g, purity 45%, 7.48 mmol) in toluene (80 ml) in a reactor equipped with a Dean-Stark destilator was added pyridinium p-toluene sulfonate (1.88 g, 7.48 g) and the reaction mixture was stirred at 120° C. for 3 days. The crude was diluted with ethyl acetate and washed with water and brine, dried over magnesium sulphate and the solvent was removed to give 7.39 g (100% yield) of the final product as a dark oil. Estimated purity 46%. This crude was used in the next step without further purification.

Workup

  1. washwashed with water and brine
  2. dry with materialdried over magnesium sulphate
  3. customthe solvent was removed

Sources & evidence

ORD record
ord-235edc5386f4419990f7e9ae28bef6d5
Source dataset
uspto-grants-2016_07
Patent number
US09388189B2

Reaction notes

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