Pyridine → HCID 19739879, compound

HRID 2255145Notes

Reaction equation

HRID 2255145 reaction equation
[OH:1][NH:2][CH:3]([CH2:7][C:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[NH:10][CH:9]=1)[C:4]([NH2:6])=[O:5].[C:17](Cl)(=[O:21])[C:18]([CH3:20])=O.N1C=CC=CC=1>CN(C)C(=O)N(C)C>[OH:1][N:2]1[CH:3]([CH2:7][C:8]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[NH:10][CH:9]=2)[C:4](=[O:5])[N:6]=[C:18]([CH3:20])[C:17]1=[O:21]

Participants

5

Reactant 3

HCID 1049PyridineHCID 5217912-Oxopropanoyl chlorideHCID 13944421HCID 13944421, compound

Product 1

HCID 19739879HCID 19739879, compoundYield 15.7%

Reagents, catalysts & solvents 1

HCID 12437TetramethylureaSolvent2×

Procedure

In 5 ml of tetramethylurea was dissolved 0.22 g of 2-hydroxylamino-3-(indol-3-yl)propionic acid amide. The solution was cooled to -5° to 0° C. Thereto was added 0.1 g of pyruvic acid chloride. Then, there was added 1 ml of a tetramethylurea solution containing 90 mg of pyridine. The mixture was stirred for 1.5 hours with ice cooling and for 1 hour at room temperature. The mixture was poured into ice water. The resulting mixture was subjected to extraction with CHCL3. The extract was washed with water, dried over magnesium sulfate, and subjected to TLC (methanol/CH2Cl2 =1/10). The fraction separated was heated for 10-20 minutes at 80° C. under vacuum. The residue was mixed with methanol for crystallization. The resulting crystals were recrystallized from methanol to obtain 40 mg of colorless needle-like cyrstals. Yield: 15%. MS (m/e):M30 271. Melting point: 166°-168° C.

Workup

  1. temperatureThe solution was cooled to -5° to 0° C
  2. extractionThe resulting mixture was subjected to extraction with CHCL3
  3. washThe extract was washed with water
  4. dry with materialdried over magnesium sulfate
  5. customThe fraction separated
  6. temperaturewas heated for 10-20 minutes at 80° C. under vacuum
  7. additionThe residue was mixed with methanol for crystallization
  8. customThe resulting crystals were recrystallized from methanol

Sources & evidence

ORD record
ord-fbd5dd0f9b6a48bfb9ed8ef5711e807c
Source dataset
uspto-grants-1993_08
Patent number
US05238938

Reaction notes

Loading…