Hydrochloric Acid → 3-(n-((2-(2-Carboxyphenyl)phenyl)carbonyl)-n-(2-(4-ethoxyphenyl)ethyl)amino)propanoic acidethyl ester

HRID 1594185Notes

Reaction equation

HRID 1594185 reaction equation
ClC1C=CC(CNC(C2C=CC=CC=2C2C=CC=CC=2C([N:24]([CH2:35][CH2:36][C:37]([OH:39])=[O:38])[CH2:25][CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=2OC)=O)=O)=CC=1.[C:42]12[C:49]3=[CH:50][CH:51]=[CH:52][CH:53]=[C:48]3[C:47](=[O:54])[O:46][C:44](=[O:45])[C:43]1=[CH:55][CH:56]=[CH:57][CH:58]=2.[CH2:59](N(CC)CC)[CH3:60].Cl.[C:67](OCC)(=[O:69])[CH3:68]>C(Cl)Cl>[CH2:59]([O:39][C:37](=[O:38])[CH2:36][CH2:35][N:24]([C:47]([C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][C:49]=1[C:42]1[CH:58]=[CH:57][CH:56]=[CH:55][C:43]=1[C:44]([OH:46])=[O:45])=[O:54])[CH2:25][CH2:26][C:27]1[CH:28]=[CH:29][C:30]([O:69][CH2:67][CH3:68])=[CH:31][CH:32]=1)[CH3:60]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 72794Diphenic anhydrideHCID 230791343-(n-((2-(2-((4-Chlorobenzylamino)carbonyl)phenyl)phenyl)carbonyl)-n-(2-(2-methoxyphenyl)ethyl)amino)propanoic acid

Product 1

HCID 692464633-(n-((2-(2-Carboxyphenyl)phenyl)carbonyl)-n-(2-(4-ethoxyphenyl)ethyl)amino)propanoic acidethyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The compound prepared in reference example 1 (600 mg), diphenic anhydride (538 mg) and triethylamine (0.85 ml) were dissolved in methylene chloride (10 ml) and the mixture was stirred overnight at room temperature. The reaction mixture was poured into a mixture of ethyl acetate and 1N hydrochloric acid, and the aqueous layer was extracted with ethyl acetate. The combined organic layer was washed with a saturated aqueous solution of sodium bicarbonate and brine successively and dried over anhydrous sodium sulfate. The solvent was evaporated to give the title compound (837 mg) having the following physical data.

Workup

  1. extractionthe aqueous layer was extracted with ethyl acetate
  2. washThe combined organic layer was washed with a saturated aqueous solution of sodium bicarbonate and brine successively
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was evaporated

Sources & evidence

ORD record
ord-2eeb114e530a41dfb41d22137bc8dde7
Source dataset
uspto-grants-2007_11
Patent number
US07300917B2

Reaction notes

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