Hydrochloric Acid → (+/-) 1-(3-Acetylthio-2-acetylthiomethyl-1-oxopropyl)-1,2,3,4-tetrahydro-2-quinolinecarboxylic Acid

HRID 1462909노트

반응식

HRID 1462909 반응식
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]

참가 물질

5

반응물 3

HCID 313Hydrochloric AcidHCID 129261603-Acetylthio-2-acetylthiomethylpropionyl chlorideHCID 457901311,2,3,4-Tetrahydroquinoline-2-carboxylic acid hydrochloride

생성물 1

HCID 13336756(+/-) 1-(3-Acetylthio-2-acetylthiomethyl-1-oxopropyl)-1,2,3,4-tetrahydro-2-quinolinecarboxylic Acid

시약·촉매·용매 1

HCID 1049Pyridine용매

실험 절차

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°.

후처리

  1. extractionThe mixture was extracted with ether
  2. extractionthe ether extract
  3. dry with materialdried over sodium sulfate
  4. customevaporated to a syrup
  5. 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)

출처 및 근거

ORD 기록
ord-ed5e7293cbf049a8ba5ea7dfad9732a7
출처 데이터셋
uspto-grants-1984_07
특허 번호
US04461896

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