Hydrochloric Acid → HCID 11261353, compound

HRID 493484Notes

Reaction equation

HRID 493484 reaction equation
[OH-].[Na+].C[O:4][C:5](=[O:39])[CH2:6][O:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[CH:19]=[CH:18][C:17]([CH2:20][N:21]([C:23]([C:25]3[C:29]4[CH:30]=[CH:31][CH:32]=[CH:33][C:28]=4[O:27][C:26]=3[CH2:34][CH2:35][CH2:36][CH3:37])=[O:24])[CH3:22])=[CH:16][CH:15]=2)=[CH:10][C:9]=1[Br:38].O.Cl>CO>[Br:38][C:9]1[CH:10]=[C:11]([C:14]2[CH:15]=[CH:16][C:17]([CH2:20][N:21]([C:23]([C:25]3[C:29]4[CH:30]=[CH:31][CH:32]=[CH:33][C:28]=4[O:27][C:26]=3[CH2:34][CH2:35][CH2:36][CH3:37])=[O:24])[CH3:22])=[CH:18][CH:19]=2)[CH:12]=[CH:13][C:8]=1[O:7][CH2:6][C:5]([OH:39])=[O:4]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 131727449HCID 131727449, compound

Product 1

HCID 11261353HCID 11261353, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1 N NaOH (2.14 mL, 2.14 mmol) was added under nitrogen to a solution of methyl[(3-bromo-4′-{[[(2-butyl-1-benzofuran-3-yl)carbonyl](methyl)amino]methyl}-1,1′-biphenyl-4-yl)oxy]acetate (1.00 g, 1.78 mmol), prepared in the previous step, in 50 mL of methanol plus 5 mL of water at room temperature. After the addition the reaction was stirred at room temperature for 4 h. The reaction was acidified by the addition of 2.5 mL of 1 N HCl and then concentrated under reduced pressure to remove most of the methanol. The solid present was collected by filtration, rinsed with water and dried under reduced pressure to give the title compound (932 mg, 100%) as a light brown solid, mp 72-78° C. Elemental Analysis for C29H28BrNO5.0.15 H2O. Calc'd: C, 62.97; H, 5.16; N, 2.53. Found: C, 62.71; H, 5.19; N, 2.39

Workup

  1. customat room temperature
  2. additionAfter the addition the reaction
  3. concentrationconcentrated under reduced pressure
  4. customto remove most of the methanol
  5. filtrationThe solid present was collected by filtration
  6. washrinsed with water
  7. customdried under reduced pressure

Sources & evidence

ORD record
ord-4ebae3429767436da565efe8a045fe29
Source dataset
uspto-grants-2009_05
Patent number
US07534894B2

Reaction notes

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