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1,2-Dichloroethane → (+/-)-trans-7-acetylamino-3-bromo-3,4-dihydro-6-nitro-2,2-dimethyl-4-[(S)-(-)-3-acetylthio-2-methylpropionyloxy]-2H-1-benzopyran

HRID 373342
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HRID 373342 반응식
[C:1]([NH:4][C:5]1[C:18]([N+:19]([O-:21])=[O:20])=[CH:17][C:8]2[C@@H:9]([OH:16])[C@H:10]([Br:15])[C:11]([CH3:14])([CH3:13])[O:12][C:7]=2[CH:6]=1)(=[O:3])[CH3:2].C(Cl)CCl.[C:26]([S:29][CH2:30][C@H:31]([CH3:35])[C:32](Cl)=[O:33])(=[O:28])[CH3:27]>N1C=CC=CC=1>[C:1]([NH:4][C:5]1[C:18]([N+:19]([O-:21])=[O:20])=[CH:17][C:8]2[C@@H:9]([O:16][C:32](=[O:33])[C@H:31]([CH3:35])[CH2:30][S:29][C:26](=[O:28])[CH3:27])[C@H:10]([Br:15])[C:11]([CH3:14])([CH3:13])[O:12][C:7]=2[CH:6]=1)(=[O:3])[CH3:2]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 111,2-DichloroethaneHCID 10954137S-(3-Chloro-2-methyl-3-oxopropyl) (S)-ethanethioateHCID 70466339(+/-)-trans-7-acetylamino-3-bromo-4-hydroxy-3,4-dihydro-6-nitro-2,2-dimethyl-2H-1-benzopyran

생성물 1

HCID 86745231(+/-)-trans-7-acetylamino-3-bromo-3,4-dihydro-6-nitro-2,2-dimethyl-4-[(S)-(-)-3-acetylthio-2-methylpropionyloxy]-2H-1-benzopyran

시약·촉매·용매 1

HCID 1049
Pyridine
용매

실험 절차

To a mixture of (±)-trans-7-acetylamino-3-bromo-4-hydroxy-3,4-dihydro-6-nitro-2,2-dimethyl-2H-1-benzopyran, ethylene chloride and pyridine was added (S)-(-)-3-acetylthio-2-methylpropionyl chloride under ice-cooling over 5 minutes and stirred for 1.5 hours under room temperature. The reaction mixture was washed with diluted hydrochloric acid once and 10% aqueous sodium chloride solution twice. The organic layer was separated, dried over magnesium sulfate and concentrated under reduced pressure to give (±)-trans-7-acetylamino-3-bromo-3,4-dihydro-6-nitro-2,2-dimethyl-4-[(S)-(-)-3-acetylthio-2-methylpropionyloxy]-2H-1-benzopyran.

후처리

  1. temperaturecooling over 5 minutes
  2. washThe reaction mixture was washed with diluted hydrochloric acid once
  3. customThe organic layer was separated
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-f5cb105da43d47e29ac4e2a57fee9a5c
출처 데이터셋
uspto-grants-1992_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05162553

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