Chloride → HCID 69137736, compound

HRID 1357300Notes

Reaction equation

HRID 1357300 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:14]=[C:15]([Cl:17])[CH:16]=1)[O:5][C:6]1[O:10][C:9]([C:11](Cl)=[O:12])=[CH:8][CH:7]=1.[Br:18][C:19]1[C:28]([O:29][CH:30]([C:38]([O:40][CH3:41])=[O:39])[CH2:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)=[CH:27][CH:26]=[C:25]2[C:20]=1[CH:21]=[CH:22][C:23]([CH2:42][NH3+:43])=[CH:24]2.[Cl-].C(N(CC)CC)C>C(Cl)Cl>[CH3:41][O:40][C:38](=[O:39])[CH:30]([O:29][C:28]1[CH:27]=[CH:26][C:25]2[C:20](=[CH:21][CH:22]=[C:23]([CH2:42][NH:43][C:11]([C:9]3[O:10][C:6]([O:5][C:4]4[CH:3]=[C:2]([Cl:1])[CH:16]=[C:15]([Cl:17])[CH:14]=4)=[CH:7][CH:8]=3)=[O:12])[CH:24]=2)[C:19]=1[Br:18])[CH2:31][C:32]1[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1

Participants

6

Reactant 4

HCID 312ChlorideHCID 8471TriethylamineHCID 27360285-(3,5-Dichlorophenoxy)furan-2-carbonyl chlorideHCID 185052915-Bromo-6-(1-methoxycarbonyl-2-phenyl-ethoxy)-naphthalen-2-ylmethyl-ammonium

Product 1

HCID 69137736HCID 69137736, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

5-(3,5-Dichloro-phenoxy)-furan-2-carbonyl chloride (0.194 g, 0.6655 mmol) was added under nitrogen to a suspension of 5-bromo-6-(1-methoxycarbonyl-2phenyl-ethoxy)-naphthalen-2-ylmethyl-ammonium; chloride (0.30 g, 0.6655 mmol), prepared in the previous step, in 20 mL of methylene chloride at room temperature. Triethylamine (0.186 mL, 1.33 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% NaHCO3. The organic layer was separated, dried (MgSO4) and the solvent removed under reduced pressure to give 2-[1-bromo-6-({[5-(3,5-dichloro-phenoxy)-furan-2-carbonyl]-amino}-methyl)-naphthalen-2-yloxy]-3-phenyl-propionic acid methyl ester (0.4079 g, 92%) as a tan oil, MS m/z: 668 [M+H]+.

Workup

  1. extractionextracted one time with 1N HCl and two times with 5% NaHCO3
  2. customThe organic layer was separated
  3. dry with materialdried (MgSO4)
  4. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-f8484a8ccd1b4a46baa0b1961eab054a
Source dataset
uspto-grants-2003_07
Patent number
US06589970B2

Reaction notes

Loading…