Water → HCID 10283127, compound

HRID 1357301Notes

Reaction equation

HRID 1357301 reaction equation
C[O:2][C:3](=[O:42])[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[O:28][C:29]([O:32][C:33]4[CH:38]=[C:37]([Cl:39])[CH:36]=[C:35]([Cl:40])[CH:34]=4)=[CH:30][CH:31]=3)=[O:26])[CH:19]=2)[C:14]=1[Br:41])[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[OH-].[Na+].O>CO>[Br:41][C:14]1[C:15]2[C:20](=[CH:19][C:18]([CH2:23][NH:24][C:25]([C:27]3[O:28][C:29]([O:32][C:33]4[CH:38]=[C:37]([Cl:39])[CH:36]=[C:35]([Cl:40])[CH:34]=4)=[CH:30][CH:31]=3)=[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:42])=[O:2]

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 69137736HCID 69137736, compound

Product 1

HCID 10283127HCID 10283127, compoundYield 27.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 2-[1-bromo-6-({[5-(3,5-dichloro-phenoxy)-furan-2-carbonyl]-amino}-methyl)-naphthalen-2-yloxy]-3-phenyl-propionic acid methyl ester (0.34 g, 0.508 mmol), prepared in the previous step, 1N NaOH (1.50 mL, 1.5 mmol), 5 mL of water and 50 mL of methanol was stirred under nitrogen at room temperature for 18 h (overnight). The methanol was removed under reduced pressure. The solid that formed was collected by filtration and identified as the sodium salt salt of 2-[1-bromo-6-({[5-(3,5-dichloro-phenoxy)-furan-2-carbonyl]-amino}-methyl)-naphthalen-2-yloxy]-3-phenyl-propionic acid (0.1537 g, 46%). The clear filtrate was acidified with 1N HCl. The solid that precipitated was collected by filtration and dried under reduced pressure to give the title compound (0.0905 g, 27%) as a white solid, mp 86-100° C.

Workup

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

Sources & evidence

ORD record
ord-6eb84cf3f2ff4862aeca32868f5605e4
Source dataset
uspto-grants-2003_07
Patent number
US06589970B2

Reaction notes

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