Phosphorus oxychloride → HCID 58574583, compound

HRID 1619335Notes

Reaction equation

HRID 1619335 reaction equation
[NH2:1][C:2]1[CH:10]=[C:9]([Br:11])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.[CH3:12][CH:13]1[CH2:18][NH:17][C:16](=O)[CH2:15][N:14]1[C:20]([O:22][CH2:23][CH:24]1[C:36]2[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=2[C:30]2[C:25]1=[CH:26][CH:27]=[CH:28][CH:29]=2)=[O:21].P(Cl)(Cl)(Cl)=O>O1CCOCC1>[Br:11][C:9]1[CH:10]=[C:2]2[C:3]([C:4](=[O:6])[N:17]3[CH2:18][CH:13]([CH3:12])[N:14]([C:20]([O:22][CH2:23][CH:24]4[C:36]5[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=5[C:30]5[C:25]4=[CH:26][CH:27]=[CH:28][CH:29]=5)=[O:21])[CH2:15][C:16]3=[N:1]2)=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 886912-Amino-4-bromobenzoic acidHCID 58574408HCID 58574408, compound

Product 1

HCID 58574583HCID 58574583, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of 2-amino-4-bromobenzoic acid (2.8 g, 13.1 mmol, 1.1 equiv), (9H-fluoren-9-yl)methyl 2-methyl-5-oxopiperazine-1-carboxylate (4 g, 11.9 mmol, 1 equiv), and phosphoryl trichloride (4 mL) in 1,4-dioxane (100 mL) was stirred at 80° C. for two hours. After it was cooled to room temperature, the reaction mixture was quenched with water and extracted with ethyl acetate (3×100 mL). The combined organic layers were dried over Na2SO4. After filtration and concentration, the residue was purified by silica gel chromatography to give the desired product.

Workup

  1. customthe reaction mixture was quenched with water
  2. extractionextracted with ethyl acetate (3×100 mL)
  3. dry with materialThe combined organic layers were dried over Na2SO4
  4. filtrationAfter filtration and concentration
  5. customthe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-15f57db3de43446ca6ea340f8f9b62c4
Source dataset
uspto-grants-2014_07
Patent number
US08772301B2

Reaction notes

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