Potassium Hydroxide → JWH 250 N-pentanoic acid metabolite

HRID 61311Notes

Reaction equation

HRID 61311 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH2:9][C:10]([C:12]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[N:14]([CH2:21][CH2:22][CH2:23][CH2:24][C:25]([O:27]CC)=[O:26])[CH:13]=1)=[O:11].[OH-].[K+]>O>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH2:9][C:10]([C:12]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[N:14]([CH2:21][CH2:22][CH2:23][CH2:24][C:25]([OH:27])=[O:26])[CH:13]=1)=[O:11]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 86691093Ethyl 5-(3-(2-(2-methoxyphenyl)acetyl)-1H-indol-1-yl)pentanoate2×

Product 1

HCID 86691092JWH 250 N-pentanoic acid metaboliteYield 71%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Ethyl 5-(3-(2-(2-methoxyphenyl)acetyl)-1H-indol-1-yl)pentanoate [Ethyl N-(carboxybutyrate) JWH-250] 7 (856 mg, 2.18 mmol) was dissolved in tertahydrofuran (15 ml) and water (15 ml) was added followed by potassium hydroxide (287 mg, 4.36 mmol). The reaction mixture was stirred at room temperature overnight. The solvent was removed in vacuo, the residue was acidified to pH 3 and extracted three times with ethyl acetate (3×50 ml). The organic fractions were combined, dried over sodium sulphate and concentrated under vacuo. The residue was purified by column chromatography (silica gel, 50%-100% ethyl acetate in hexane) and then recrystalised from ethylacetate/hexane to give 565 mg (71%) 5-(3-(2-(2-methoxyphenyl)acetyl)-1H-indol-1-yl)pentanoic acid [N-(carboxybutyric acid) JWH-250] (Hapten 2) as a white solid.

Workup

  1. additionwas added
  2. customThe solvent was removed in vacuo
  3. extractionextracted three times with ethyl acetate (3×50 ml)
  4. dry with materialdried over sodium sulphate
  5. concentrationconcentrated under vacuo
  6. customThe residue was purified by column chromatography (silica gel, 50%-100% ethyl acetate in hexane)
  7. customrecrystalised from ethylacetate/hexane

Sources & evidence

ORD record
ord-a7e6ed454f594540b59bfe29c1ded721
Source dataset
uspto-grants-2016_09
Patent number
US09441033B2

Reaction notes

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