methyl 2-{[6-(1-benzyl-5-phenyl-1H-pyrrol-2-yl)-2-naphthyl]oxy}-3-phenylpropanoate → 2-{[6-(1-Benzyl-5-phenyl-1H-pyrrol-2-yl)-2-naphthyl]oxy}-3-phenylpropanoic acid

HRID 456819Notes

Reaction equation

HRID 456819 reaction equation
[CH2:1]([N:8]1[C:12]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:11][CH:10]=[C:9]1[C:19]1[CH:20]=[C:21]2[C:26](=[CH:27][CH:28]=1)[CH:25]=[C:24]([O:29][CH:30]([CH2:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)[C:31]([O:33]C)=[O:32])[CH:23]=[CH:22]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>O>[CH2:1]([N:8]1[C:12]([C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)=[CH:11][CH:10]=[C:9]1[C:19]1[CH:20]=[C:21]2[C:26](=[CH:27][CH:28]=1)[CH:25]=[C:24]([O:29][CH:30]([CH2:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)[C:31]([OH:33])=[O:32])[CH:23]=[CH:22]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 1

HCID 18439043methyl 2-{[6-(1-benzyl-5-phenyl-1H-pyrrol-2-yl)-2-naphthyl]oxy}-3-phenylpropanoate

Product 1

HCID 116565842-{[6-(1-Benzyl-5-phenyl-1H-pyrrol-2-yl)-2-naphthyl]oxy}-3-phenylpropanoic acidYield 90%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

In a similar manner as described in step 7 of Example 1, the title compound was prepared from methyl 2-{[6-(1-benzyl-5-phenyl-1H-pyrrol-2-yl)-2-naphthyl]oxy}-3-phenylpropanoate (0.145 g, 0.270 mmol), prepared in the previous step, and the addition of water (3 mL) to the reaction mixture. After the volatiles were removed under reduced pressure, the residue was partitioned between water and methylene chloride. The layers were separated and the aqueous layer was extracted one time with methylene chloride. The combined extracts were dried (MgSO4), filtered and the solvent removed under reduced pressure to give the title compound as an off-white solid (0.127 g, 90%), mp 70–80° C. Elemental Analysis for C36H29NO3.0.48 H2O Calc'd: C, 81.23; H, 5.67; N, 2.63. Found: C, 80.67; H 6.28; N, 2.36.

Workup

  1. customprepared in the previous step
  2. customAfter the volatiles were removed under reduced pressure
  3. customthe residue was partitioned between water and methylene chloride
  4. customThe layers were separated
  5. extractionthe aqueous layer was extracted one time with methylene chloride
  6. dry with materialThe combined extracts were dried (MgSO4)
  7. filtrationfiltered
  8. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-fba7a89705f547f58e8ee32c2cf0590b
Source dataset
uspto-grants-2007_03
Patent number
US07186749B2

Reaction notes

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