Water → HCID 21866659, compound

HRID 857222Notes

Reaction equation

HRID 857222 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH2:8][CH:9]([C:20]([OH:22])=O)[NH:10][C:11]([C:13]2[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][CH:14]=2)=[O:12])[CH:3]=1.[C:23](OC(=O)C)(=O)C.O>N1C=CC=CC=1>[C:20]([CH:9]([NH:10][C:11]([C:13]1[CH:14]=[CH:15][C:16]([CH3:19])=[CH:17][CH:18]=1)=[O:12])[CH2:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([Br:1])[CH:3]=1)(=[O:22])[CH3:23]

Participants

5

Reactant 3

HCID 962WaterHCID 7918Acetic AnhydrideHCID 21866969HCID 21866969, compound

Product 1

HCID 21866659HCID 21866659, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
92.5 °C

Procedure

1-Bromo-3-[2-carboxy-2-(p-toluoylamino)ethyl]benzene (16.84 g) was dissolved in 85 ml of pyridine, and 55 ml of acetic anhydride was added and stirred for 3 hours under argon atmosphere at 90-95° C. Water (55 ml) was added dropwise gradually so that the maximum temperature did not exceed 100° C., and the mixture was stirred for 20 minutes at 60-70° C. The reaction solution was cooled, poured into ice-cold water and extracted with ethyl acetate. The resulting solution was washed with 10% hydrochloric acid, water and saturated aqueous sodium hydrogen carbonate solution sequentially and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure. The resulting crystals were washed with isopropyl ether to provide 13.31 g of the objective compound as brownish crystals. M.p. 106-107° C.

Workup

  1. customdid not exceed 100° C.
  2. stirringthe mixture was stirred for 20 minutes at 60-70° C
  3. temperatureThe reaction solution was cooled
  4. additionpoured into ice-cold water
  5. extractionextracted with ethyl acetate
  6. washThe resulting solution was washed with 10% hydrochloric acid, water and saturated aqueous sodium hydrogen carbonate solution sequentially
  7. dry with materialdried over anhydrous magnesium sulfate
  8. distillationThe solvent was distilled off under reduced pressure
  9. washThe resulting crystals were washed with isopropyl ether

Sources & evidence

ORD record
ord-a2d37600a07548fa853491bdb164c73c
Source dataset
uspto-grants-2006_12
Patent number
US07144906B2

Reaction notes

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