Hydrochloric Acid → 3-[Methyl(8-{2-[(2-phenylacetyl)amino]ethyl}-2-naphthyl)amino]propanoic Acid

HRID 985771Notes

Reaction equation

HRID 985771 reaction equation
C([O-])([O-])=O.[K+].[K+].[CH3:7][N:8]([C:16]1[CH:25]=[CH:24][C:23]2[C:18](=[C:19]([CH2:26][CH2:27][NH:28][C:29](=[O:37])[CH2:30][C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[CH:20]=[CH:21][CH:22]=2)[CH:17]=1)[CH2:9][CH2:10][C:11]([O:13]CC)=[O:12].Cl>CO>[CH3:7][N:8]([C:16]1[CH:25]=[CH:24][C:23]2[C:18](=[C:19]([CH2:26][CH2:27][NH:28][C:29](=[O:37])[CH2:30][C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[CH:20]=[CH:21][CH:22]=2)[CH:17]=1)[CH2:9][CH2:10][C:11]([OH:13])=[O:12]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 21917049Ethyl 3-{methyl-[8-(2-{[2-phenylacetyl]amino}ethyl)-2-naphthyl]amino}propanoate

Product 1

HCID 219171333-[Methyl(8-{2-[(2-phenylacetyl)amino]ethyl}-2-naphthyl)amino]propanoic Acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

An aqueous 0.5N solution of K2CO3 (10 ml) is added to the product obtained in Step A (4 mmol) dissolved in methanol (10 ml). When the reaction has ceased, the solution is acidified to pH 6-7 using 1N hydrochloric acid solution. The reaction mixture is extracted with dichloromethane. The organic phase is washed with water, dried over magnesium sulphate and concentrated under reduced pressure. The residue is chromatographed on silica gel to yield the title product.

Workup

  1. extractionThe reaction mixture is extracted with dichloromethane
  2. washThe organic phase is washed with water
  3. dry with materialdried over magnesium sulphate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue is chromatographed on silica gel

Sources & evidence

ORD record
ord-1e1ff129adba410a925699e4ee6d7896
Source dataset
uspto-grants-2005_03
Patent number
US06872851B1

Reaction notes

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