Hydrochloric Acid → HCID 12083577, compound

HRID 1357282Notes

Reaction equation

HRID 1357282 reaction equation
[OH-].[Na+].C[O:4][C:5](=[O:45])[CH:6]([CH2:38][C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)[CH2:7][O:8][C:9]1[CH:18]=[CH:17][C:16]2[C:11](=[CH:12][CH:13]=[C:14]([CH2:19][N:20]([C:22]([C:24]3[O:25][C:26]4[CH:36]=[CH:35][CH:34]=[CH:33][C:27]=4[C:28]=3[CH2:29][CH2:30][CH2:31][CH3:32])=[O:23])[CH3:21])[CH:15]=2)[C:10]=1[Br:37].O.Cl>CO>[CH2:38]([CH:6]([CH2:7][O:8][C:9]1[CH:18]=[CH:17][C:16]2[C:11](=[CH:12][CH:13]=[C:14]([CH2:19][N:20]([C:22]([C:24]3[O:25][C:26]4[CH:36]=[CH:35][CH:34]=[CH:33][C:27]=4[C:28]=3[CH2:29][CH2:30][CH2:31][CH3:32])=[O:23])[CH3:21])[CH:15]=2)[C:10]=1[Br:37])[C:5]([OH:45])=[O:4])[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium Hydroxide2×HCID 69137773HCID 69137773, compound

Product 1

HCID 12083577HCID 12083577, compoundYield 42%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 1 N NaOH (2.5 mL, 2.5 mmol) and 2-benzyl-3-(1-bromo-6-{[(3-butyl-benzofuran-2-carbonyl)-methyl-amino]-methyl}-naphthalen-2-yloxy)-propionic acid methyl ester (769 mg, 1.22 mmol), prepared in the previous step, in 30 mL of methanol plus 2 mL of water was stirred under nitrogen at room temperature for 6 h. By TLC starting material remained. An additional 2.5 mL (2.5 mmol) of 1 N NaOH was added and the stirring continued at room temperature overnight. 1 N HCl (5.1 mL, 5.1 mmol) was added and the reaction 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 (318 mg, 42%) as a white solid, mp 64-68° C.

Workup

  1. concentrationthe reaction concentrated under reduced pressure
  2. customto remove the methanol
  3. customThe solid that formed
  4. filtrationwas collected by filtration
  5. customdried under reduced pressure

Sources & evidence

ORD record
ord-8ac3a094423947519fb60ae9ef6fb8ff
Source dataset
uspto-grants-2003_07
Patent number
US06589970B2

Reaction notes

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