Hydrochloric Acid → Methyl 2-chloro-5-[3-(2-methoxy-4-(5-phenylpentyloxy)phenyl)propanoylamino]benzoate

HRID 349245

Reaction equation

HRID 349245 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:6]=[CH:5][C:4]=1[CH2:21][CH2:22][C:23]([OH:25])=O.Cl.C(N=C=NCCCN(C)C)C.[Cl:38][C:39]1[CH:48]=[CH:47][C:46]([NH2:49])=[CH:45][C:40]=1[C:41]([O:43][CH3:44])=[O:42].CN(C1C=CC=CN=1)C.Cl>C(N(CC)CC)C.CN(C)C=O>[Cl:38][C:39]1[CH:48]=[CH:47][C:46]([NH:49][C:23](=[O:25])[CH2:22][CH2:21][C:4]2[CH:5]=[CH:6][C:7]([O:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=3)=[CH:8][C:3]=2[O:2][CH3:1])=[CH:45][C:40]=1[C:41]([O:43][CH3:44])=[O:42]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 218852-DimethylaminopyridineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 5200412Methyl 5-Amino-2-chlorobenzoateHCID 691318743-[2-Methoxy-4-(5-phenylpentyloxy)phenyl]propanoic acid

Product 1

HCID 58804649Methyl 2-chloro-5-[3-(2-methoxy-4-(5-phenylpentyloxy)phenyl)propanoylamino]benzoateYield 58.9%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

To a mixture of 3-[2-methoxy-4-(5-phenylpentyloxy)phenyl]propanoic acid (342 mg), 1-ethyl-3-[3-(dimethylamino)propyl]carbodiimide hydrochloride (288 mg), 1-hydroxybenzotriazole-1-hydrate (153 mg) and dimethylformamide (5 mL) was added methyl 2-chloro-5-aminobenzoate (265 mg) and triethylamine (0.7 mL). To the reaction mixture was added dimethylaminopyridine (50 mg). The reaction mixture was stirred at room temperature overnight. 1N hydrochloric acid was added to the reaction mixture, which was extracted with ethyl acetate. The extract was washed with saturated aqueous solution of sodium hydrogen carbonate and brine, dried over an anhydrous sodium sulfate and concentrated. The obtained residue was purified by column chromatography on silica gel (hexane:ethyl acetate=4:1) to give the title compound (300 mg) having the following physical data.

Workup

  1. extractionwas extracted with ethyl acetate
  2. washThe extract was washed with saturated aqueous solution of sodium hydrogen carbonate and brine
  3. dry with materialdried over an anhydrous sodium sulfate
  4. concentrationconcentrated
  5. customThe obtained residue was purified by column chromatography on silica gel (hexane:ethyl acetate=4:1)

Sources & evidence

ORD record
ord-51e6c4e70d1742679be2953da10b47a2
Source dataset
uspto-grants-2007_02
Patent number
US07179817B2

Linked notes

Loading…