Potassium Carbonate → HCID 22010226, compound

HRID 322898Notes

Reaction equation

HRID 322898 reaction equation
C[O:2][C:3]([CH:5]([NH:13][C:14]([C:16]1[CH:37]=[CH:36][C:35]([O:38][CH2:39][C:40]2[CH:44]=[CH:43][S:42][CH:41]=2)=[CH:34][C:17]=1[O:18][CH:19]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1[CH3:33])[CH2:20][CH2:21][C:22]([O:24]CC)=[O:23])=[O:15])[CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[O:4].C(=O)([O-])[O-].[K+].[K+]>CO>[C:3]([CH:5]([NH:13][C:14]([C:16]1[CH:37]=[CH:36][C:35]([O:38][CH2:39][C:40]2[CH:44]=[CH:43][S:42][CH:41]=2)=[CH:34][C:17]=1[O:18][CH:19]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1[CH3:33])[CH2:20][CH2:21][C:22]([OH:24])=[O:23])=[O:15])[CH2:6][C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1)([OH:4])=[O:2]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 23204058HCID 23204058, compound

Product 1

HCID 22010226HCID 22010226, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of ethyl 4-[2-(1-methoxycarbonyl-2-phenylethylcarbamoyl)-5-(3-thienylmethoxy)phenoxy]-4-(2-methylphenyl)butanoate, thought to be the diastereomers (1R, 4RS), (0.48 g) in methanol (100 mL) is treated with 10% aqueous potassium carbonate solution (10 mL). The reaction mixture is stirred at room temperature for 18 hours and evaporated. The residue is dissolved in water (50 mL), the solution acidified to pH 1 by addition of 1 N hydrochloric acid and extracted with ethyl acetate (120 mL). The organic phase is washed with water (100 mL), brine (100 mL), dried over magnesium sulphate and evaporated. The semi-solid residue (0.44 g) is boiled with acetonitrile (20 mL), the mixture cooled to room temperature and filtered to remove 2-[2-hydroxy-4-(3-thienylmethoxy)benzoylamino]-3-phenylpropionic acid (0.047 g) as a white solid, m.p. 178-180° C. [Elemental analysis:- C,63.52; H,4.76; N,3.15%. Calculated :- C,63.46; H,4.82; N,3.52%]. The filtrate is evaporated to give 4-[2-(1-carboxy-2-phenylethylcarbamoyl)-5-(3-thienylmethoxy)phenoxy]-4-(2-methylphenyl)butanoic acid, thought to be the diastereomers (1R, 4RS), (0.3 g), as an oily semi-solid. [Elemental analysis:- C,66.54; H,5.45; N,2.35%. Calculated :- C,67.00; H,5.45; N,2.44%].

Workup

  1. customevaporated
  2. dissolutionThe residue is dissolved in water (50 mL)
  3. additionthe solution acidified to pH 1 by addition of 1 N hydrochloric acid
  4. extractionextracted with ethyl acetate (120 mL)
  5. washThe organic phase is washed with water (100 mL), brine (100 mL)
  6. dry with materialdried over magnesium sulphate
  7. customevaporated
  8. temperaturethe mixture cooled to room temperature
  9. filtrationfiltered
  10. customto remove 2-[2-hydroxy-4-(3-thienylmethoxy)benzoylamino]-3-phenylpropionic acid (0.047 g) as a white solid, m.p. 178-180° C. [Elemental analysis:- C,63.52; H,4.76; N,3.15%. Calculated :- C,63.46; H,4.82; N,3.52%]
  11. customThe filtrate is evaporated

Sources & evidence

ORD record
ord-1f3d73c6a07f412db60a9c82712bdbd7
Source dataset
uspto-grants-2001_04
Patent number
US06211234B1

Reaction notes

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