Water → HCID 10167270, compound

HRID 1357222Notes

Reaction equation

HRID 1357222 reaction equation
C[O:2][C:3](=[O:40])[CH:4]([O:12][C:13]1[CH:22]=[CH:21][C:20]2[C:15](=[CH:16][CH:17]=[C:18]([NH:23][C:24]([C:26]3[C:30]4[CH:31]=[CH:32][CH:33]=[CH:34][C:29]=4[O:28][C:27]=3[CH2:35][CH2:36][CH2:37][CH3:38])=[O:25])[CH:19]=2)[C:14]=1[Br:39])[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[OH-].[Na+].O>CO>[Br:39][C:14]1[C:15]2[C:20](=[CH:19][C:18]([NH:23][C:24]([C:26]3[C:30]4[CH:31]=[CH:32][CH:33]=[CH:34][C:29]=4[O:28][C:27]=3[CH2:35][CH2:36][CH2:37][CH3:38])=[O:25])=[CH:17][CH:16]=2)[CH:21]=[CH:22][C:13]=1[O:12][CH:4]([CH2:5][C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1)[C:3]([OH:40])=[O:2]

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium Hydroxide2×HCID 69139119HCID 69139119, compound

Product 1

HCID 10167270HCID 10167270, compoundYield 81.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 2-{1-bromo-6-[(2-butyl-benzofuran-3-carbonyl)-amino]-naphthalen-2-yloxy}-3-phenyl-propionic acid methyl ester (139 mg, 0.231 mmol), prepared in the previous step, and 1 N NaOH (231 μL, 0.231 mmol) in 75 mL of methanol was refluxed for 4 h. By TLC starting material remained. Water (10 mL) and 1 N NaOH (231 μL, 0.231 mmol) were added and the mixture refluxed for 18 h (overnight). The reaction was filtered and 2 mL of 1 N HCL was added to the filtrate. The filtrate was concentrated under reduced pressure to remove the methanol. The solid formed was collected by filtration, rinsed with water and dried under reduced pressure to give the title compound (111 mg, 81%) as a white solid, mp 191-195° C.

Workup

  1. temperaturewas refluxed for 4 h
  2. temperaturethe mixture refluxed for 18 h (overnight)
  3. filtrationThe reaction was filtered
  4. addition2 mL of 1 N HCL was added to the filtrate
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. customto remove the methanol
  7. customThe solid formed
  8. filtrationwas collected by filtration
  9. washrinsed with water
  10. customdried under reduced pressure

Sources & evidence

ORD record
ord-753564790f854f94b7b54c9012022886
Source dataset
uspto-grants-2003_07
Patent number
US06589970B2

Reaction notes

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