Chloride → 2-(1-Bromo-6-{[(2-ethyl-benzofuran-3-carbonyl)-amino]-methyl}-naphthalen-2-yloxy)-3-phenyl-propionic acid methyl ester

HRID 1357303Notes

Reaction equation

HRID 1357303 reaction equation
[CH2:1]([C:3]1[O:4][C:5]2[CH:14]=[CH:13][CH:12]=[CH:11][C:6]=2[C:7]=1[C:8](Cl)=[O:9])[CH3:2].[Br:15][C:16]1[C:25]([O:26][CH:27]([C:35]([O:37][CH3:38])=[O:36])[CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[CH:24][CH:23]=[C:22]2[C:17]=1[CH:18]=[CH:19][C:20]([CH2:39][NH3+:40])=[CH:21]2.[Cl-].C(N(CC)CC)C>C(Cl)Cl>[CH3:38][O:37][C:35](=[O:36])[CH:27]([O:26][C:25]1[CH:24]=[CH:23][C:22]2[C:17](=[CH:18][CH:19]=[C:20]([CH2:39][NH:40][C:8]([C:7]3[C:6]4[CH:11]=[CH:12][CH:13]=[CH:14][C:5]=4[O:4][C:3]=3[CH2:1][CH3:2])=[O:9])[CH:21]=2)[C:16]=1[Br:15])[CH2:28][C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1

Participants

6

Reactant 4

HCID 312ChlorideHCID 8471TriethylamineHCID 185052915-Bromo-6-(1-methoxycarbonyl-2-phenyl-ethoxy)-naphthalen-2-ylmethyl-ammoniumHCID 185052952-Ethyl-benzofuran-3-carbonyl chloride

Product 1

HCID 691385692-(1-Bromo-6-{[(2-ethyl-benzofuran-3-carbonyl)-amino]-methyl}-naphthalen-2-yloxy)-3-phenyl-propionic acid methyl esterYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

2-Ethyl-benzofuran-3-carbonyl chloride (0.444 mmol), prepared in step 2 of Example 21, was added under nitrogen to a suspension of 5-bromo-6-(1-methoxycarbonyl-2-phenyl-ethoxy)-naphthalen-2-ylmethyl-ammonium; chloride (0.200 g, 0.444 mmol), prepared in step 3 of Example 53, in 20 mL of methylene chloride. Triethylamine (0.124 mL, 0.888 mmol) was then added to the mixture. The reaction was stirred at room temperature for 18 h (overnight). The reaction was diluted with methylene chloride, extracted one time with 1N HCl and two times with 5% sodium bicarbonate. The organic layer was separated, dried (MgSO4) and the solvent removed under reduced pressure to give 2-(1-bromo-6-{[(2-ethyl-benzofuran-3-carbonyl)-amino]-methyl}-naphthalen-2-yloxy)-3-phenyl-propionic acid methyl ester (0.27 g, 100%) as a tan solid, mp 139-143° C.

Workup

  1. extractionextracted one time with 1N HCl and two times with 5% sodium bicarbonate
  2. customThe organic layer was separated
  3. dry with materialdried (MgSO4)
  4. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-70dd9c1c53d94c899ce6631ca448c631
Source dataset
uspto-grants-2003_07
Patent number
US06589970B2

Reaction notes

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