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

HRID 1246410Notes

Reaction equation

HRID 1246410 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-04fdc42828f54d709283bd7ab443fb5d
Source dataset
uspto-grants-2006_10
Patent number
US07126012B2

Reaction notes

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