Potassium Hydroxide → JWH 250 N-pentanoic acid metabolite

HRID 61311ノート

反応式

HRID 61311 の反応式
[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]

参加物

4

反応物 2

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

生成物 1

HCID 86691092JWH 250 N-pentanoic acid metabolite収率 71%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-a7e6ed454f594540b59bfe29c1ded721
出典データセット
uspto-grants-2016_09
特許番号
US09441033B2

反応ノート

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