Hydrochloric Acid → HCID 11330095, compound

HRID 493477Notes

Reaction equation

HRID 493477 reaction equation
C[O:2][C:3](=[O:36])[CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH:17]=[CH:16][C:15]([CH2:18][NH:19][C:20]([C:22]3[C:26]4[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=4[O:24][C:23]=3[CH2:31][CH2:32][CH2:33][CH3:34])=[O:21])=[CH:14][CH:13]=2)=[CH:8][C:7]=1[Br:35].O.[OH-].[Na+].Cl>CO>[Br:35][C:7]1[CH:8]=[C:9]([C:12]2[CH:13]=[CH:14][C:15]([CH2:18][NH:19][C:20]([C:22]3[C:26]4[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=4[O:24][C:23]=3[CH2:31][CH2:32][CH2:33][CH3:34])=[O:21])=[CH:16][CH:17]=2)[CH:10]=[CH:11][C:6]=1[O:5][CH2:4][C:3]([OH:36])=[O:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 131727448HCID 131727448, compound

Product 1

HCID 11330095HCID 11330095, compoundYield 88.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methyl{[3-bromo-4′-({[(2-butyl-1-benzofuran-3-yl)carbonyl]amino}methyl)[1,1′-biphenyl]-4-yl]oxy}acetate (314 mg, 0.57 mmol), prepared in the previous step, in 100 mL of methanol and 10 mL of water was warmed to dissolve the solid. While still warm 1 N NaOH (684 μL, 0.68 mmol) was added and the mixture stirred, with no additional heat, until the reaction was complete by TLC. The reaction was acidified by the addition of 715 μL of 1 N HCl and then concentrated under reduced pressure to remove the methanol. The solid that formed was collected by filtration and dried under reduced pressure to give the title compound as a light tan solid (270 mg, 87%), mp 175-190° C. Elemental Analysis for C28H26BrNO5.0.40 H2O. Calc'd: C, 61.87; H, 4.97; N, 2.58. Found: C, 61.35; H, 4.54; N, 2.51.

Workup

  1. dissolutionto dissolve the solid
  2. concentrationconcentrated under reduced pressure
  3. customto remove the methanol
  4. customThe solid that formed
  5. filtrationwas collected by filtration
  6. customdried under reduced pressure

Sources & evidence

ORD record
ord-d5f151cfef7b4c53bafbe586e44c025a
Source dataset
uspto-grants-2009_05
Patent number
US07534894B2

Reaction notes

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