Trifluoroacetic acid → (2-Trifluoromethyl-7,8-dihydro-3H-6,9-dioxa-1,3-diazacyclopenta[a]naphthalen-8-yl)methyl 4-methylbenzenesulfonate

HRID 1368355노트

반응식

HRID 1368355 반응식
Cl.Cl.[CH3:3][C:4]1[CH:9]=[CH:8][C:7]([S:10]([O:13][CH2:14][C@@H:15]2[O:20][C:19]3[C:21]([NH2:26])=[C:22]([NH2:25])[CH:23]=[CH:24][C:18]=3[O:17][CH2:16]2)(=[O:12])=[O:11])=[CH:6][CH:5]=1.[F:27][C:28]([F:33])([F:32])[C:29](O)=O>C(Cl)Cl>[CH3:3][C:4]1[CH:9]=[CH:8][C:7]([S:10]([O:13][CH2:14][CH:15]2[O:20][C:19]3[C:18](=[CH:24][CH:23]=[C:22]4[NH:25][C:29]([C:28]([F:33])([F:32])[F:27])=[N:26][C:21]4=3)[O:17][CH2:16]2)(=[O:12])=[O:11])=[CH:6][CH:5]=1

참가 물질

4

반응물 2

HCID 6422Trifluoroacetic acidHCID 86586513[(2R)-7,8-diamino-2,3-dihydro-1,4-benzodioxin-2-yl]methyl 4-methylbenzenesulfonate dihydrochloride

생성물 1

HCID 22341388(2-Trifluoromethyl-7,8-dihydro-3H-6,9-dioxa-1,3-diazacyclopenta[a]naphthalen-8-yl)methyl 4-methylbenzenesulfonate

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

A solution of 3.1 g (7.3 mmole) of [(2R)-7,8-diamino-2,3-dihydro-1,4-benzodioxin-2-yl]methyl 4-methylbenzenesulfonate dihydrochloride in 50 mL of trifluoroacetic acid was refluxed under nitrogen for 6 hours. The mixture was diluted to 400 mL with methylene chloride, washed with 400 mL of water and with 400 mL of saturated aqueous sodium bicarbonate, dried over magnesium sulfate, filtered and concentrated to a crude foam in vacuum. The crude product was column chromatographed on silica gel with 1% methanol in chloroform and the product fractions combined and concentrated in vacuum to give 3.3 g of the (R)-enantiomer of the title compound as a white solid, m.p. 114-116° C., which retains one equivalent of chloroform.

후처리

  1. washwashed with 400 mL of water and with 400 mL of saturated aqueous sodium bicarbonate
  2. dry with materialdried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated to a crude foam in vacuum
  5. customchromatographed on silica gel with 1% methanol in chloroform
  6. concentrationconcentrated in vacuum

출처 및 근거

ORD 기록
ord-5447ce272bab4da7a80bba24cf312a28
출처 데이터셋
uspto-grants-2003_06
특허 번호
US06573283B2

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