Hydrochloric Acid → HCID 10167602, compound

HRID 1357234Notes

Reaction equation

HRID 1357234 reaction equation
[OH-].[Na+].C[O:4][C:5](=[O:43])[CH:6]([O:14][C:15]1[CH:24]=[CH:23][C:22]2[C:17](=[CH:18][CH:19]=[C:20]([CH2:25][NH:26][C:27]([C:29]3[C:33]4[CH:34]=[CH:35][CH:36]=[CH:37][C:32]=4[O:31][C:30]=3[CH2:38][CH2:39][CH2:40][CH3:41])=[O:28])[CH:21]=2)[C:16]=1[Br:42])[CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.O.Cl>CO>[Br:42][C:16]1[C:17]2[C:22](=[CH:21][C:20]([CH2:25][NH:26][C:27]([C:29]3[C:33]4[CH:34]=[CH:35][CH:36]=[CH:37][C:32]=4[O:31][C:30]=3[CH2:38][CH2:39][CH2:40][CH3:41])=[O:28])=[CH:19][CH:18]=2)[CH:23]=[CH:24][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:43])=[O:4]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium Hydroxide2×HCID 69137597HCID 69137597, compound

Product 1

HCID 10167602HCID 10167602, compoundYield 59.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1 N Sodium hydroxide (220 μL, 0.22 mmol) was added under nitrogen to a solution of 2-(1-bromo-6-{[(2-butyl-benzofuran-3-carbonyl)-amino]-methyl}-naphthalen-2-yloxy)-3-phenyl-propionic acid methyl ester (107 mg, 0.17 mmol), prepared in the previous step, in 40 mL of methanol plus 10 mL of water at room temperature. After the addition the reaction was stirred at room temperature overnight. By TLC starting material remained. Additional quantities of 1 N NaOH were added until the reaction was complete by TLC. The reaction was acidified by the addition of 1 N HCl and then concentrated under reduced pressure to remove the methanol. The solid formed was collected by filtration and dried under reduced pressure to give the title compound (61 mg, 58%) as a white solid, mp 125-130° C.

Workup

  1. customat room temperature
  2. additionAfter the addition the reaction
  3. concentrationconcentrated under reduced pressure
  4. customto remove the methanol
  5. customThe solid formed
  6. filtrationwas collected by filtration
  7. customdried under reduced pressure

Sources & evidence

ORD record
ord-59742e4e8ea74f9488dd0c57c8aa7806
Source dataset
uspto-grants-2003_07
Patent number
US06589970B2

Reaction notes

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