p-Toluenesulfonic acid → HCID 67176599, compound

HRID 2362195Notes

Reaction equation

HRID 2362195 reaction equation
COC(=O)CC.NC1C=CC(C(N)=O)=CC=1C.C([O:20][C:21](=[O:39])[CH2:22][CH2:23][C:24](=[O:38])[CH2:25][CH2:26][C:27]([C:29]1[CH:34]=[CH:33][C:32]([C:35](=[O:37])[NH2:36])=[CH:31][CH:30]=1)=[O:28])C.C1(C)C=CC(S(O)(=O)=O)=CC=1>CCO.ClCCl>[C:35]([C:32]1[CH:31]=[CH:30][C:29]([C:27](=[O:28])[CH2:26][CH2:25][C:24](=[O:38])[CH2:23][CH2:22][C:21]([OH:39])=[O:20])=[CH:34][CH:33]=1)(=[O:37])[NH2:36]

Participants

7

Reactant 4

HCID 6101p-Toluenesulfonic acidHCID 11124Methyl propionateHCID 121180574-amino-3-methylbenzamideHCID 67177553HCID 67177553, compound

Product 1

HCID 67176599HCID 67176599, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Procedure

Synthesis of 3-[1-carbamoyl-2-methyl-phenyl)-5-(4-carbamoyl-phenyl)-1H-pyrrole-2-yl]-propanoic acid methyl ester. 4-amino-3-methyl benzamide (20 mg, 0.13 mmol) was added to 7-(4-carbamoyl-phenyl)-4,7-dioxo-heptanoic acid ethyl ester mixture (˜0.11 mmol) in EtOH, followed by the addition of p-toluenesulfonic acid (2 mg, 0.01 mmol). The resultant mixture was heated at 80° C. for 12 hours. The residue of the crude reaction mixture was dissolved in dichloromethane and then purified by silica-gel chromatography using 5% methanol in chloroform as the solvent system (5 mg; product: 3-[1-carbamoyl-2-methyl-phenyl)-5-(4-carbamoyl-phenyl)-1H-pyrrole-2-yl]-propanoic acid methyl ester).

Workup

  1. customThe residue of the crude reaction mixture
  2. custompurified by silica-gel chromatography

Sources & evidence

ORD record
ord-81123ef168cf4f75b1b66f110553bdb7
Source dataset
uspto-grants-2014_04
Patent number
US08691816B2

Reaction notes

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