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Triethylamine → 2-(tert-butyl) 4-ethyl 3-methyl-5-(3-((methylsulfonyl)oxy)propyl)-1H-pyrrole-2,4-dicarboxylate

HRID 2191397
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HRID 2191397 반응식
[CH2:1]([O:3][C:4]([C:6]1[C:7]([CH3:22])=[C:8]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[NH:9][C:10]=1[CH2:11][CH2:12][CH2:13][OH:14])=[O:5])[CH3:2].C(N(CC)CC)C.[CH3:30][S:31](Cl)(=[O:33])=[O:32]>ClCCl>[CH2:1]([O:3][C:4]([C:6]1[C:7]([CH3:22])=[C:8]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[NH:9][C:10]=1[CH2:11][CH2:12][CH2:13][O:14][S:31]([CH3:30])(=[O:33])=[O:32])=[O:5])[CH3:2]
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참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 498403932-O-tert-butyl 4-O-ethyl 5-(3-hydroxypropyl)-3-methyl-1H-pyrrole-2,4-dicarboxylate

생성물 1

HCID 592500502-(tert-butyl) 4-ethyl 3-methyl-5-(3-((methylsulfonyl)oxy)propyl)-1H-pyrrole-2,4-dicarboxylate수율 99%

시약·촉매·용매 1

HCID 6344Dichloromethane
용매

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온도
-10 °C

실험 절차

5-(3-Hydroxy-propyl)-3-methyl-1H-pyrrole-2,4-dicarboxylic acid 2-tert-butyl ester 4-ethyl ester 1f (9.20 g, 30 mmol) was dissolved in 150 ml of dichloromethane under stirring, and added with triethylamine (7.0 ml, 50 mmol) to the solution while maintaining the temperature at about −10° C. in an ice-salt bath under an argon atmosphere. Upon completion of the addition, the mixture was added slowly with methanesulfonyl chloride (3.5 ml, 45 mmol). After stirring to mix well, the reaction system was allowed to warm up to room temperature and stirred for 4 hours. After thin lay chromatography showed the disappearance of starting materials, the reaction mixture was quenched with ice. The reaction mixture was washed successively with dilute hydrochloric acid (0.5 mol/L, 80 ml×2) to remove triethylamine, saturated sodium carbonate solution (80 ml×2) to remove excess hydrochloric acid and saturated brine (80 ml), and concentrated under reduced pressure to obtain the title compound 5-(3-methanesulfonyloxy-propyl)-3-methyl-1H-pyrrole-2,4-dicarboxylic acid 2-tert-butyl ester 4-ethyl ester 1 g (11.4 g, yield 99%) as a brown oil.

후처리

  1. additionUpon completion of the addition
  2. stirringAfter stirring
  3. additionto mix well
  4. temperatureto warm up to room temperature
  5. stirringstirred for 4 hours
  6. customthe reaction mixture was quenched with ice
  7. washThe reaction mixture was washed successively with dilute hydrochloric acid (0.5 mol/L, 80 ml×2)
  8. customto remove triethylamine, saturated sodium carbonate solution (80 ml×2)
  9. customto remove excess hydrochloric acid and saturated brine (80 ml)
  10. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-f2eb12cf204e45d19f2440e33611f315
출처 데이터셋
uspto-grants-2012_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08329682B2

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