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Chloride → HCID 69138717, compound

HRID 1357302
Notes
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Reaction equation

HRID 1357302 reaction equation
[CH:1]1([C:7]2[CH:15]=[CH:14][C:10]([C:11](Cl)=[O:12])=[CH:9][CH:8]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[Br:16][C:17]1[C:26]([O:27][CH:28]([C:36]([O:38][CH3:39])=[O:37])[CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)=[CH:25][CH:24]=[C:23]2[C:18]=1[CH:19]=[CH:20][C:21]([CH2:40][NH3+:41])=[CH:22]2.[Cl-].C(N(CC)CC)C>C(Cl)Cl>[CH3:39][O:38][C:36](=[O:37])[CH:28]([O:27][C:26]1[CH:25]=[CH:24][C:23]2[C:18](=[CH:19][CH:20]=[C:21]([CH2:40][NH:41][C:11](=[O:12])[C:10]3[CH:14]=[CH:15][C:7]([CH:1]4[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]4)=[CH:8][CH:9]=3)[CH:22]=2)[C:17]=1[Br:16])[CH2:29][C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 312ChlorideHCID 8471TriethylamineHCID 185052915-Bromo-6-(1-methoxycarbonyl-2-phenyl-ethoxy)-naphthalen-2-ylmethyl-ammoniumHCID 218908474-Cyclohexylbenzoyl chloride

Product 1

HCID 69138717HCID 69138717, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 6344
Dichloromethane
Solvent
2×

Procedure

4-Cyclohexyl-benzoyl chloride (0.67 mmol) was added under nitrogen to a suspension of 5-bromo-6-(1-methoxycarbonyl-2-phenyl-ethoxy)-naphthalen-2-ylmethyl-ammonium; chloride (0.30 g, 0.67 mmol), prepared in step 3 of Example 53, in 20 mL of methylene chloride at room temperature. Triethylamine (0.186 mL, 1.33 mmol) was then added to the mixture. After the addition 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-[(4-cyclohexyl-benzoylamino)-methyl]-naphthalen-2-yloxyl}-3-phenyl-propionic acid methyl ester (0.3362 g, 84%) as an off-white solid, mp 160-161° C.

Workup

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

Sources & evidence

ORD record
ord-a3edc5ab721b4bd692df1204552f9669
Source dataset
uspto-grants-2003_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06589970B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes