Glycine → HCID 57423718, compound

HRID 1725178Notes

Reaction equation

HRID 1725178 reaction equation
[CH2:1]([NH:3][C:4](=[O:23])[C:5]1[CH:10]=[CH:9][C:8]([C:11](=O)[CH2:12][CH2:13][C:14](=O)[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:7][CH:6]=1)[CH3:2].[NH2:24][CH2:25][C:26]([OH:28])=[O:27]>C(O)(=O)C>[CH2:1]([NH:3][C:4]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[N:24]([CH2:25][C:26]([OH:28])=[O:27])[C:14]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[CH:13][CH:12]=2)=[CH:7][CH:6]=1)=[O:23])[CH3:2]

Participants

4

Reactant 2

HCID 750GlycineHCID 57423717HCID 57423717, compound

Product 1

HCID 57423718HCID 57423718, compoundYield 34.4%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a slurry of ˜1.0 mmol ethyl benzamide from Step 3 in 3 mL acetic acid was added 0.15 g (2.0 mmol) glycine. The reaction was mixed at 90-102° C. for 5.5 hr and allowed to cool. The solution was concentrated and and the residue was purified by 6Gilson preparative HPLC to afford 120 mg of [2-(4-ethylcarbamoyl-phenyl)-5-phenyl-pyrrol-1-yl]-acetic acid [5LC-MS data molecular ion and retention time): m/z 349 (M+H); 2.36 min] as a brown solid.

Workup

  1. additionThe reaction was mixed at 90-102° C. for 5.5 hr
  2. temperatureto cool
  3. concentrationThe solution was concentrated
  4. customthe residue was purified by 6Gilson preparative HPLC

Sources & evidence

ORD record
ord-ee02e595675b4fdda588ae8c4b4486d3
Source dataset
uspto-grants-2009_02
Patent number
US07488832B2

Reaction notes

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