Sodium Hydroxide → HCID 67233870, compound

HRID 2362216Notes

Reaction equation

HRID 2362216 reaction equation
C([O:3][C:4](=[O:34])[CH2:5][CH2:6][C:7]1[N:8]([C:24]2[CH:29]=[CH:28][C:27]([C:30](=[O:32])[NH2:31])=[CH:26][C:25]=2[CH3:33])[C:9]([C:12]2[CH:17]=[CH:16][C:15]([C:18]([O:20][CH3:21])=[O:19])=[CH:14][C:13]=2[O:22][CH3:23])=[CH:10][CH:11]=1)C.[OH-].[Na+]>CO>[C:30]([C:27]1[CH:28]=[CH:29][C:24]([N:8]2[C:9]([C:12]3[CH:17]=[CH:16][C:15]([C:18]([O:20][CH3:21])=[O:19])=[CH:14][C:13]=3[O:22][CH3:23])=[CH:10][CH:11]=[C:7]2[CH2:6][CH2:5][C:4]([OH:34])=[O:3])=[C:25]([CH3:33])[CH:26]=1)(=[O:32])[NH2:31]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 67234642HCID 67234642, compound

Product 1

HCID 67233870HCID 67233870, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

3-[1-(4-Carbamoyl-2-methylphenyl)-5-(4-methoxycarbonylmethoxy-phenyl)-1H-pyrrol-2-yl]-propionic acid ethyl ester 16B (57 mg, 0.12 mmol) was dissolved in 1 mL methanol. 1 N NaOH (0.25 mL, 0.25 mmol.) was added. After 18 hrs, the reaction was concentrated in vacuo and diluted with water. The pH was adjusted to 1 with 1 M HCl and extracted with EtOAc (3×4 mL). The combined organic layers were dried over Na2SO4, filtered and concentrated in vacuo. The residue was triturated with hexanes and dried under high vacuum to yield 3-[1-(4-Carbamoyl-2-methylphenyl)-5-(4-methoxycarbonyl-methoxyphenyl)-1H-pyrrol-2-yl]-propionic acid (16C) (34 mg, 65%, light yellow powder).

Workup

  1. concentrationthe reaction was concentrated in vacuo
  2. additiondiluted with water
  3. extractionextracted with EtOAc (3×4 mL)
  4. dry with materialThe combined organic layers were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was triturated with hexanes
  8. customdried under high vacuum

Sources & evidence

ORD record
ord-605a320448794c12bba0bea97c5143c1
Source dataset
uspto-grants-2014_04
Patent number
US08691816B2

Reaction notes

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