Pyridine → HCID 54249407, compound

HRID 1720646Notes

Reaction equation

HRID 1720646 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][CH:5]([CH2:9][C:10]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH:13]=[CH:12][CH:11]=1)[C:6]([OH:8])=[O:7].[C:20]1([CH3:30])[CH:25]=[CH:24][C:23]([S:26](Cl)(=[O:28])=[O:27])=[CH:22][CH:21]=1.N1C=CC=[CH:33][CH:32]=1>>[C:10]1([CH2:9][CH:5]([CH2:4][CH2:3][CH2:2][O:1][S:26]([C:23]2[CH:24]=[CH:25][C:20]([CH3:30])=[CH:21][CH:22]=2)(=[O:28])=[O:27])[C:6]([O:8][CH2:32][CH3:33])=[O:7])[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH:13]=[CH:12][CH:11]=1.[C:10]1([CH2:9][CH:5]([CH2:4][CH2:3][CH2:2][O:1][S:26]([C:23]2[CH:24]=[CH:25][C:20]([CH3:30])=[CH:21][CH:22]=2)(=[O:28])=[O:27])[C:6]([O:8][CH3:32])=[O:7])[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH:13]=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 73974-Toluenesulfonyl chlorideHCID 22418885HCID 22418885, compound

Product 2

HCID 54249407HCID 54249407, compoundHCID 54336881HCID 54336881, compound

Procedure

2.31 g of the mixture of the ethyl ester and methyl ester of (2RS)-5-hydroxy-2-(1-naphthylmethyl)pentanoic acid was dissolved in 35 ml of dry pyridine, and 1.69 g of p-toluenesulfonyl chloride was added thereto. The mixture was stirred at room temperature overnight. The reaction solution was concentrated under reduced pressure, and 200 ml of ethyl acetate was added to the residue. The ethyl acetate layer was washed with a 5% potassium hydrogensulfate aqueous solution, with a 5% sodium hydrogencarbonate aqueous solution and with a saturated sodium chloride aqueous solution and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure and the residue was purified by silica gel column chromatography (n-hexane/ethyl acetate=5/1) to obtain 643 mg of ethyl (2RS)-2-(1-naphthylmethyl)-5-p-toluenesulfonyloxypentanoate, 184 mg of methyl (2RS)-2-(1-naphthylmethyl)-5-p-toluenesulfonyloxypentanoate and 650 mg of a mixture of the two compounds.

Workup

  1. concentrationThe reaction solution was concentrated under reduced pressure, and 200 ml of ethyl acetate
  2. additionwas added to the residue
  3. washThe ethyl acetate layer was washed with a 5% potassium hydrogensulfate aqueous solution, with a 5% sodium hydrogencarbonate aqueous solution and with a saturated sodium chloride aqueous solution
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationThe solvent was distilled off under reduced pressure
  6. customthe residue was purified by silica gel column chromatography (n-hexane/ethyl acetate=5/1)

Sources & evidence

ORD record
ord-e0fbe942ef1b4b6885e1aba675160dc7
Source dataset
uspto-grants-1996_04
Patent number
US05506356

Reaction notes

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