Hydrochloric Acid → (+/-) 1-(3-Acetylthio-2-acetylthiomethyl-1-oxopropyl)-1,2,3,4-tetrahydro-2-quinolinecarboxylic Acid
反応式
Cl.[NH:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH2:5][CH2:4][CH:3]1[C:12]([OH:14])=[O:13].[C:15]([S:18][CH2:19][CH:20]([CH2:24][S:25][C:26](=[O:28])[CH3:27])[C:21](Cl)=[O:22])(=[O:17])[CH3:16].Cl>N1C=CC=CC=1>[C:15]([S:18][CH2:19][CH:20]([CH2:24][S:25][C:26](=[O:28])[CH3:27])[C:21]([N:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH2:5][CH2:4][CH:3]1[C:12]([OH:14])=[O:13])=[O:22])(=[O:17])[CH3:16]参加物
5
反応物 3
生成物 1
試薬・触媒・溶媒 1
実験手順
A solution of (±)-1,2,3,4-tetrahydro-2-quinolinecarboxylic acid hydrochloride (14.52 g) in pyridine (150 ml) was treated dropwise with 3-acetylthio-2-(acetylthiomethyl)propanoyl chloride with vigorous stirring. After stirring overnight at room temperature, the mixture was added to ice (300 g) and the pH was adjusted to 2.5 with concentrated hydrochloric acid. The mixture was extracted with ether and the ether extract dried over sodium sulfate and evaporated to a syrup. This (±) 1-(3-acetylthio-2-acetylthiomethyl-1-oxopropyl)-1,2,3,4-tetrahydro-2-quinolinecarboxylic acid was further purified by column chromatography (silica gel, toluene:ethyl acetate:acetic acid, 6.5:3:0.5); yield 2.5 g, m.p. 149°-151°.
後処理
- extractionThe mixture was extracted with ether
- extractionthe ether extract
- dry with materialdried over sodium sulfate
- customevaporated to a syrup
- customThis (±) 1-(3-acetylthio-2-acetylthiomethyl-1-oxopropyl)-1,2,3,4-tetrahydro-2-quinolinecarboxylic acid was further purified by column chromatography (silica gel, toluene:ethyl acetate:acetic acid, 6.5:3:0.5)
出典と根拠
- ORDレコード
- ord-ed5e7293cbf049a8ba5ea7dfad9732a7
- 出典データセット
- uspto-grants-1984_07
- 特許番号
- US04461896
反応ノート
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