Hydrochloric Acid → HCID 58305604, compound

HRID 2362208Notes

Reaction equation

HRID 2362208 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]2[C:14]([C:15]3[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=3)=[CH:13][CH:12]=[C:11]2[CH2:22][CH2:23][C:24]([OH:26])=[O:25])=[C:6]([CH3:27])[CH:5]=1)(=[O:3])[NH2:2].C(=O)([O-])[O-].[K+].[K+].Br[CH2:35][C:36]([NH2:38])=[O:37].Cl>O.CN(C)C=O>[C:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]2[C:14]([C:15]3[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=3)=[CH:13][CH:12]=[C:11]2[CH2:22][CH2:23][C:24]([OH:26])=[O:25])=[C:6]([CH3:27])[CH:5]=1)(=[O:3])[NH2:2].[NH2:38][C:36](=[O:37])[CH2:35][O:21][C:18]1[CH:19]=[CH:20][C:15]([C:14]2[N:10]([C:7]3[CH:8]=[CH:9][C:4]([C:1](=[O:3])[NH2:2])=[CH:5][C:6]=3[CH3:27])[C:11]([CH2:22][CH2:23][C:24]([OH:26])=[O:25])=[CH:12][CH:13]=2)=[CH:16][CH:17]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 696322-BromoacetamideHCID 46174364HCID 46174364, compound

Product 2

HCID 46174364HCID 46174364, compoundHCID 58305604HCID 58305604, compoundYield 61.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

3-(1-(4-carbamoyl-2-methylphenyl)-5-(4-hydroxyphenyl)-1H-pyrrol-2-yl)propanoic acid (7A, R1=4-carbamoyl-2-methylphenyl) was prepared according to the methodology shown in Scheme 1, R2=4-hydroxyphenyl, R1=4-carbamoyl-2-methylphenyl. A N,N-dimethylformamide solution of 3-(1-(4-carbamoyl-2-methylphenyl)-5-(4-hydroxyphenyl)-1H-pyrrol-2-yl)propanoic acid (36 mg, 0.1 mmol, 1 ml), potassium carbonate (27 mg, 0.2 mmol) and 2-bromoacetamide (18 mg, 0.12 mmol) was stirred for 18 hrs at ambient temperature, after which time the reaction was diluted with water and the pH adjusted to 2 with 1 M HCl. The aqueous layer was extracted with EtOAc (3×3 mL), dried over N2SO4, filtered and concentrated in vacuo. The residue thus obtained was triturated with hexanes and dried under high vacuum to yield the title compound as a light yellow powder (13 mg).

Workup

  1. extractionThe aqueous layer was extracted with EtOAc (3×3 mL)
  2. customdried over N2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue thus obtained
  6. customwas triturated with hexanes
  7. customdried under high vacuum

Sources & evidence

ORD record
ord-8dece31914db42b182425506002ceab9
Source dataset
uspto-grants-2014_04
Patent number
US08691816B2

Reaction notes

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