Potassium Carbonate → HCID 178430803, compound

HRID 852306Notes

Reaction equation

HRID 852306 reaction equation
[OH:1][CH2:2][C@@H:3]([NH:10][C:11]([C:13]1[NH:14][CH:15]=[C:16]([C:18](=O)[C:19]([CH2:24]OC)=[CH:20]N(C)C)[CH:17]=1)=[O:12])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[NH2:28][C:29]([NH2:31])=[S:30].C(=O)([O-])[O-].[K+].[K+]>C(O)C>[OH:1][CH2:2][C@@H:3]([NH:10][C:11]([C:13]1[NH:14][CH:15]=[C:16]([C:18]2[C:19]([CH3:24])=[CH:20][N:31]=[C:29]([SH:30])[N:28]=2)[CH:17]=1)=[O:12])[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 2723790ThioureaHCID 865879764-(3-Dimethylamino-2-methoxymethyl-acryloyl)-1H-pyrrole-2-carboxylic Acid (2-hydroxy-1-(S)-phenyl-ethyl)-amide

Product 1

HCID 178430803HCID 178430803, compoundYield 48.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
90 °C

Procedure

4-(3-Dimethylamino-2-methoxymethyl-acryloyl)-1H-pyrrole-2-carboxylic acid (2-hydroxy-1-(S)-phenyl-ethyl)-amide (17.6 mmol, 6.0 g) was combined with thiourea (39 mmol, 3.0 g) and potassium carbonate (53 mmol, 7.3 g) in ethanol (50 mL) and the resulting suspension was heated at 90° C. for 24 hrs. The solvent was removed in vacuo and the resulting black solid was diluted with water and the solid was removed by filtration. The solid was washed with ethyl acetate twice and the aqueous solution was acidified to pH 5–6 with HCl (2N). The solid formed was removed by filtration and the aqueous solution was then extracted twice with ethyl acetate. The combined organic phases were dried over sodium sulfate. The solvent was removed under vacuum to afford the title compound as a brown solid (3.0 g, 48% yield). HPLC Method B, Rt=3.7 minutes, 1H NMR consistent with structure.

Workup

  1. customThe solvent was removed in vacuo
  2. additionthe resulting black solid was diluted with water
  3. customthe solid was removed by filtration
  4. washThe solid was washed with ethyl acetate twice
  5. customThe solid formed
  6. customwas removed by filtration
  7. extractionthe aqueous solution was then extracted twice with ethyl acetate
  8. dry with materialThe combined organic phases were dried over sodium sulfate
  9. customThe solvent was removed under vacuum

Sources & evidence

ORD record
ord-af5e4e143c7940bf8759e908b3547b4f
Source dataset
uspto-grants-2007_08
Patent number
US07253187B2

Reaction notes

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