Hydrochloric Acid → HCID 10282804, compound

HRID 1357247Notes

Reaction equation

HRID 1357247 reaction equation
[OH-].[Na+].C[O:4][C:5](=[O:49])[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[C:42]1[CH:47]=[CH:46][C:45]([Cl:48])=[CH:44][CH:43]=1)[CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.O.Cl>CO>[CH2:38]([C:30]1[O:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=2[C:29]=1[C:27]([NH:26][CH2:25][C:20]1[CH:21]=[C:22]2[C:17](=[CH:18][CH:19]=1)[C:16]([C:42]1[CH:47]=[CH:46][C:45]([Cl:48])=[CH:44][CH:43]=1)=[C:15]([O:14][CH:6]([CH2:7][C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[C:5]([OH:49])=[O:4])[CH:24]=[CH:23]2)=[O:28])[CH2:39][CH2:40][CH3:41]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium Hydroxide3×HCID 69137631HCID 69137631, compound

Product 1

HCID 10282804HCID 10282804, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1 N NaOH (300 μL, 0.30 mmol) was added under nitrogen to a solution of 2-[6-{[(2-butyl-benzofuran-3-carbonyl)-amino]-methyl}-1-(4-chloro-phenyl)-naphthalen-2-yloxy]-3-phenyl-propionic acid methyl ester (182 mg, 0.28 mmol), prepared in the previous step, in 30 mL of methanol plus 2.5 mL of water at room temperature. After the addition the reaction was stirred at room temperature overnight. If starting material remains additional 1 N NaOH is added until the reaction is complete. A total of 900 μL of 1 N NaOH was added. The reaction was acidified by the addition of 1.6 mL of 1 N HCl and then concentrated under reduced pressure. The solid that formed was collected by filtration and dried under reduced pressure to give the title compound (166 mg, 94%) as a white solid, mp 169-172° C.

Workup

  1. customat room temperature
  2. additionAfter the addition the reaction
  3. additionis added until the reaction
  4. concentrationconcentrated under reduced pressure
  5. customThe solid that formed
  6. filtrationwas collected by filtration
  7. customdried under reduced pressure

Sources & evidence

ORD record
ord-3f44c8dce59a4587bc013a3e3fa62014
Source dataset
uspto-grants-2003_07
Patent number
US06589970B2

Reaction notes

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