Hydrochloric Acid → HCID 45380782, 화합물

HRID 451357

반응식

HRID 451357 반응식
[CH3:1][C:2]1[C:3]([C:17]([NH:19][C:20]2[CH:25]=[CH:24][C:23]([S:26]([CH3:29])(=[O:28])=[O:27])=[CH:22][CH:21]=2)=[O:18])=[CH:4][NH:5][C:6]=1[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[C:13]([F:16])([F:15])[F:14].CC(C)([O-])C.[Na+].[CH3:36][C@H:37]1[C@H:41]([CH3:42])OS(=O)(=O)[O:38]1.Cl>CN(C)C(=O)C>[OH:38][C@@H:37]([CH3:36])[C@H:41]([N:5]1[C:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[C:13]([F:16])([F:14])[F:15])=[C:2]([CH3:1])[C:3]([C:17]([NH:19][C:20]2[CH:25]=[CH:24][C:23]([S:26]([CH3:29])(=[O:28])=[O:27])=[CH:22][CH:21]=2)=[O:18])=[CH:4]1)[CH3:42]

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 13545565133815-22-2HCID 23676156Sodium t-butoxideHCID 585388304-Methyl-N-(4-(methylsulfonyl)phenyl)-5-(2-(trifluoromethyl)phenyl)-1H-pyrrole-3-carboxamide

생성물 1

HCID 45380782HCID 45380782, 화합물수율 69%

시약·촉매·용매 1

HCID 31374Dimethylacetamide용매2회

실험 절차

To a solution of 4-methyl-N-[4-(methylsulfonyl)phenyl]-5-[2-(trifluoromethyl)phenyl]-1H-pyrrole-3-carboxamide (28 g, 66 mmol) in anhydrous N,N-dimethylacetamide (DMA) (0.53 L) was added sodium tert-butoxide (15 g, 15 mmol) and stirred at room temperature for 30 min under N2. (4S,5S)-4,5-dimethyl-1,3,2-dioxathiolane 2,2-dioxide (15 g, 99 mmol) in anhydrous DMA (2.0 ml) was added to the solution and stirred at 70° C. for 2.0 h. The reaction mixture was cooled to room temperature and added 2N HCl (0.14 L) and concentrated on a rotary evaporator. To this residue was added anhydrous tetrahydrofuran (THF) (140 ml) and 5N HCl (0.14 L) and stirred at 60° C. for 90 min. The mixture was diluted with ethyl acetate and washed with water, saturated NaHCO3 and brine, then dried over sodium sulfate and concentrated on a rotary evaporator. The resulting residue was purified by silica-gel column chromatography (9:1 to 1:1 dichloromethane:ethyl acetate) to give an atropisomeric mixture of title compound as a white solid (22.5 g, 69%).

후처리

  1. stirringstirred at 70° C. for 2.0 h
  2. temperatureThe reaction mixture was cooled to room temperature
  3. concentrationconcentrated on a rotary evaporator
  4. additionTo this residue was added anhydrous tetrahydrofuran (THF) (140 ml) and 5N HCl (0.14 L)
  5. stirringstirred at 60° C. for 90 min
  6. additionThe mixture was diluted with ethyl acetate
  7. washwashed with water, saturated NaHCO3 and brine
  8. dry with materialdried over sodium sulfate
  9. concentrationconcentrated on a rotary evaporator
  10. customThe resulting residue was purified by silica-gel column chromatography (9:1 to 1:1 dichloromethane:ethyl acetate)
  11. customto give

출처 및 근거

ORD 기록
ord-8f9bdc5e51bf4f3b977a9f899c9f11fb
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08487117B2

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