Water → HCID 11239127, compound

HRID 493486Notes

Reaction equation

HRID 493486 reaction equation
[OH-].[Na+].C[O:4][C:5](=[O:46])[CH:6]([O:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]2[CH:26]=[CH:25][C:24]([CH2:27][N:28]([C:30]([C:32]3[C:36]4[CH:37]=[CH:38][CH:39]=[CH:40][C:35]=4[O:34][C:33]=3[CH2:41][CH2:42][CH2:43][CH3:44])=[O:31])[CH3:29])=[CH:23][CH:22]=2)=[CH:17][C:16]=1[Br:45])[CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.O>CO>[Br:45][C:16]1[CH:17]=[C:18]([C:21]2[CH:26]=[CH:25][C:24]([CH2:27][N:28]([C:30]([C:32]3[C:36]4[CH:37]=[CH:38][CH:39]=[CH:40][C:35]=4[O:34][C:33]=3[CH2:41][CH2:42][CH2:43][CH3:44])=[O:31])[CH3:29])=[CH:23][CH:22]=2)[CH:19]=[CH:20][C:15]=1[O:14][CH:6]([CH2:7][C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[C:5]([OH:46])=[O:4]

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 68859788HCID 68859788, compound

Product 1

HCID 11239127HCID 11239127, compoundYield 92.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1 N NaOH (2.28 mL, 2.28 mmol) was added under nitrogen to a solution of methyl2-[(3-bromo-4′-{[[(2-butyl-1-benzofuran-3-yl)carbonyl](methyl)amino]methyl}-1,1′-biphenyl-4-yl)oxy]-3-phenylpropanoate (995 mg, 1.52 mmol), prepared in the previous step, in 100 mL of methanol plus 10 mL of water. After the addition the reaction was refluxed for 5 h. The reaction was filtered, acidified with 2.5 mL of 1 N HCl and concentrated under reduced pressure to remove the methanol. The solid that was present was collected by filtration and dried under reduced pressure to give the title compound (900 mg, 92%) as a white solid, mp 79-86° C. Elemental Analysis for C36H34BrNO5Calc'd: C, 67.50; H, 5.35; N, 2.19. Found: C, 6 7.16; H, 5.42; N, 2.09

Workup

  1. additionAfter the addition the reaction
  2. temperaturewas refluxed for 5 h
  3. filtrationThe reaction was filtered
  4. concentrationconcentrated under reduced pressure
  5. customto remove the methanol
  6. filtrationThe solid that was present was collected by filtration
  7. customdried under reduced pressure

Sources & evidence

ORD record
ord-d205a35bc15a43b3b7e1a248af1be63e
Source dataset
uspto-grants-2009_05
Patent number
US07534894B2

Reaction notes

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