Potassium Hydroxide → JWH 250 N-pentanoic acid metabolite

HRID 61311노트

반응식

HRID 61311 반응식
[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]

참가 물질

4

반응물 2

HCID 14797Potassium HydroxideHCID 86691093Ethyl 5-(3-(2-(2-methoxyphenyl)acetyl)-1H-indol-1-yl)pentanoate2회

생성물 1

HCID 86691092JWH 250 N-pentanoic acid metabolite수율 71%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-a7e6ed454f594540b59bfe29c1ded721
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09441033B2

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