Hydrochloric Acid → HCID 19367320, compound

HRID 1291573Notes

Reaction equation

HRID 1291573 reaction equation
[C:1]1([CH:7]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:8]([OH:10])=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CN(C1C=CC=CN=1)C.[CH2:26]([O:33][C:34]1[C:43]2[C:38](=[C:39]([CH2:44][CH2:45][NH2:46])[CH:40]=[CH:41][CH:42]=2)[CH:37]=[CH:36][CH:35]=1)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.Cl>C(Cl)Cl.O.C(Cl)CCl>[CH2:26]([O:33][C:34]1[C:43]2[C:38](=[C:39]([CH2:44][CH2:45][NH:46][C:8]([CH:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)=[O:10])[CH:40]=[CH:41][CH:42]=2)[CH:37]=[CH:36][CH:35]=1)[C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 8333Diphenylacetic AcidHCID 218852-DimethylaminopyridineHCID 19367325HCID 19367325, compound

Product 1

HCID 19367320HCID 19367320, compoundYield 51.6%

Reagents, catalysts & solvents 3

HCID 111,2-DichloroethaneSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of diphenylacetic acid (0.171 g) in methylene chloride (10 ml), dimethylaminopyridine (0.01 g) and 1-benzyloxy-5-(2-aminoethyl)naphthalene (0.196 g) were added at room temperature. After 10 minutes, EDC. HCl (0.154 g) was added to the mixture solution. The mixture was stirred overnight at room temperature for 1 night. After termination of reaction, water and methylene chloride were added to the reaction mixture. The organic layer was washed with a saturated aqueous solution of ammonium chloride, water and a saturated aqueous solution of sodium chloride, dried over and concentrated under reduced pressure. The residue was purified on silica gel chromatography to give the title compound (0.172 g) having the following physical data.

Workup

  1. additionwere added to the reaction mixture
  2. washThe organic layer was washed with a saturated aqueous solution of ammonium chloride, water
  3. dry with materiala saturated aqueous solution of sodium chloride, dried over and
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified on silica gel chromatography

Sources & evidence

ORD record
ord-bed614066d5f47eeaf735ab6d3a21f34
Source dataset
uspto-grants-1998_05
Patent number
US05753700

Reaction notes

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