Pyridine → HCID 1522270, compound

HRID 1855927Notes

Reaction equation

HRID 1855927 reaction equation
[NH:1]1[CH2:8][CH2:7][CH2:6][C@H:2]1[C:3]([OH:5])=[O:4].N1C=CC=CC=1.[O:15]([CH2:22][C:23](Cl)=[O:24])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>O>[O:15]([CH2:22][C:23]([N:1]1[CH2:8][CH2:7][CH2:6][C@H:2]1[C:3]([OH:5])=[O:4])=[O:24])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 69703Phenoxyacetyl chlorideHCID 145742L-Proline

Product 1

HCID 1522270HCID 1522270, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2.53 grams (g) of L-proline and 20 milliliters (ml) of anhydrous pyridine are mixed in a flask cooled by an ice bath, and 3.42 g of phenoxyacetyl chloride is added dropwise over about a 20-minute period. The mixture is warmed by water bath to room temperature, and the solvent evaporated under reduced pressure (in vacuo), leaving a viscuous syrup. The syrup is dissolved in 15 ml water and the water is evaporated in vacuo. The residue is dissolved in 20 ml water, and the resulting solution is filtered, and subsequently treated with 10 ml of 2 N hydrochloride. The resulting precipitate, crude phenoxyacetyl-L-proline, is purified on a chromatographic column containing 80 g of silica gel. The column is eluted with a solvent mixture composed of equal volumes of isopropanol and toluene to provide phenoxyacetyl-L-proline.

Workup

  1. temperaturecooled by an ice bath
  2. customthe solvent evaporated under reduced pressure (in vacuo)
  3. customleaving a viscuous syrup
  4. customthe water is evaporated in vacuo
  5. dissolutionThe residue is dissolved in 20 ml water
  6. filtrationthe resulting solution is filtered
  7. additionsubsequently treated with 10 ml of 2 N hydrochloride
  8. customThe resulting precipitate, crude phenoxyacetyl-L-proline, is purified on a chromatographic column
  9. additioncontaining 80 g of silica gel
  10. washThe column is eluted with a solvent mixture

Sources & evidence

ORD record
ord-98448a96134841d0b8305ba1a9191a09
Source dataset
uspto-grants-1980_08
Patent number
US04217269

Reaction notes

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