Glycine → HCID 57423683, compound

HRID 1725167Notes

Reaction equation

HRID 1725167 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9](=O)[CH2:10][CH2:11][C:12]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=O)=[CH:5][CH:4]=1.[NH2:21][CH2:22][C:23]([OH:25])=[O:24]>C(O)(=O)C>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:21]([CH2:22][C:23]([OH:25])=[O:24])[C:12]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)=[CH:11][CH:10]=2)=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 750GlycineHCID 28172391-(4-METHOXY-PHENYL)-4-PHENYL-BUTANE-1,4-DIONE

Product 1

HCID 57423683HCID 57423683, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 1-(4-methoxy-phenyl)-4-phenyl-butane-1,4-dione (2.90 g, 10.8 mmol) and glycine 4 (1.62 g, 21.6 mmol) in 100 mL of glacial acetic acid is heated at 100° C. The reaction is monitored by TLC, when the starting material is consumed, the mixture is washed with 5% H2SO4 (200 mL) and then extracted with ethyl acetate (2×200 mL). The organics are combined, dried over sodium sulfate, filtered and concentrated to yield [2-(4-Methoxy-phenyl)-5-phenyl-pyrrol-1-yl]-acetic acid as a green solid (3.40 g, crude), characterized by LCMS (Obs: 308.54, Cal: 307.34).

Workup

  1. customis consumed
  2. washthe mixture is washed with 5% H2SO4 (200 mL)
  3. extractionextracted with ethyl acetate (2×200 mL)
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-1e4d9b8d04dc4b7896652976d76f5f86
Source dataset
uspto-grants-2009_02
Patent number
US07488832B2

Reaction notes

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