Hydrochloric Acid → HCID 10188204, compound

HRID 1357304Notes

Reaction equation

HRID 1357304 reaction equation
C[O:2][C:3](=[O:39])[CH:4]([O:12][C:13]1[CH:22]=[CH:21][C:20]2[C:15](=[CH:16][CH:17]=[C:18]([CH2:23][NH:24][C:25]([C:27]3[C:31]4[CH:32]=[CH:33][CH:34]=[CH:35][C:30]=4[O:29][C:28]=3[CH2:36][CH3:37])=[O:26])[CH:19]=2)[C:14]=1[Br:38])[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[OH-].[Na+].O.Cl>CO>[Br:38][C:14]1[C:15]2[C:20](=[CH:19][C:18]([CH2:23][NH:24][C:25]([C:27]3[C:31]4[CH:32]=[CH:33][CH:34]=[CH:35][C:30]=4[O:29][C:28]=3[CH2:36][CH3:37])=[O:26])=[CH:17][CH:16]=2)[CH:21]=[CH:22][C:13]=1[O:12][CH:4]([CH2:5][C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1)[C:3]([OH:39])=[O:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 691385692-(1-Bromo-6-{[(2-ethyl-benzofuran-3-carbonyl)-amino]-methyl}-naphthalen-2-yloxy)-3-phenyl-propionic acid methyl ester

Product 1

HCID 10188204HCID 10188204, compoundYield 29.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 2-(1-bromo-6-{[(2-ethyl-benzofuran-3-carbonyl)-amino]-methyl}-naphthalen-2-yloxy)-3-phenyl-propionic acid methyl ester (0.200 g, 0.341 mmol), prepared in the previous step, 1N NaOH (1.02 mL, 1.02 mmol), 10 mL of water and 100 mL of methanol was stirred under nitrogen at room temperature for 20 h (overnight). The reaction was acidified with 1N HCl until acidic by litmus paper. The methanol was removed under reduced pressure. The solid that precipitated and was collected by filtration and dried under reduced pressure to give the title compound (0.0576 g, 29%) as a white solid, mp 162-165° C.

Workup

  1. customThe methanol was removed under reduced pressure
  2. customThe solid that precipitated
  3. filtrationwas collected by filtration
  4. customdried under reduced pressure

Sources & evidence

ORD record
ord-098c57c5f2d14c5ba9c925d0cde18618
Source dataset
uspto-grants-2003_07
Patent number
US06589970B2

Reaction notes

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