Potassium Carbonate → HCID 67234642, compound

HRID 2362215Notes

Reaction equation

HRID 2362215 reaction equation
[CH2:1]([O:3][C:4](=[O:29])[CH2:5][CH2:6][C:7]1[N:8]([C:19]2[CH:24]=[CH:23][C:22]([C:25](=[O:27])[NH2:26])=[CH:21][C:20]=2[CH3:28])[C:9]([C:12]2[CH:17]=[CH:16][C:15](O)=[CH:14][CH:13]=2)=[CH:10][CH:11]=1)[CH3:2].[C:30](=O)([O-])[O-:31].[K+].[K+].BrC[C:38]([O:40][CH3:41])=[O:39].[NH4+].[Cl-]>CN(C)C=O>[CH2:1]([O:3][C:4](=[O:29])[CH2:5][CH2:6][C:7]1[N:8]([C:19]2[CH:24]=[CH:23][C:22]([C:25](=[O:27])[NH2:26])=[CH:21][C:20]=2[CH3:28])[C:9]([C:12]2[CH:17]=[CH:16][C:15]([C:38]([O:40][CH3:41])=[O:39])=[CH:14][C:13]=2[O:31][CH3:30])=[CH:10][CH:11]=1)[CH3:2]

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 25517Ammonium ChlorideHCID 60984Methyl bromoacetateHCID 58305575HCID 58305575, compound

Product 1

HCID 67234642HCID 67234642, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-[1-(4-Carbamoyl-2-methylphenyl)-5-(4-hydroxyphenyl)-1H-pyrrol-2-yl]-propionic acid ethyl ester 16A (synthesized according to the first three steps of Scheme 1, where Ar2=4-hydroxyphenyl, and Ar1=4-carbamoyl-2-methylphenyl) (47 mg, 0.12 mmol) was dissolved in 0.5 mL N,N-dimethylformamide. Potassium carbonate (33 mg, 0.24 mmol) was added. Methyl 2-bromoacetate (0.02 mL, 0.13 mmol) was added. After 18 hrs, the reaction was poured into NH4Cl (sat) and extracted with EtOAc (2×5 mL). The combined organic layers were washed with brine and dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by preparative TLC plate (10% IPA/CH2Cl2). The desired band (RF=0.57) was isolated and dried under high vacuum to yield 3-[1-(4-Carbamoyl-2-methylphenyl)-5-(4-methoxycarbonyl-methoxyphenyl)-1H-pyrrol-2-yl]-propionic acid ethyl ester (16B) (57 mg, 98%, white powder).

Workup

  1. extractionextracted with EtOAc (2×5 mL)
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by preparative TLC plate (10% IPA/CH2Cl2)
  7. customThe desired band (RF=0.57) was isolated
  8. customdried under high vacuum

Sources & evidence

ORD record
ord-af2573785d334755adee9faae91321c3
Source dataset
uspto-grants-2014_04
Patent number
US08691816B2

Reaction notes

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