Trifluoromethanesulfonic anhydride → HCID 178500919, 화합물

HRID 1063622

반응식

HRID 1063622 반응식
[OH:1][CH2:2][CH2:3][C:4]([O:6][CH3:7])=[O:5].C(C1C=CC=C(C(C)(C)C)N=1)(C)(C)C.FC(F)(F)S(OS(C(F)(F)F)(=O)=O)(=O)=O.O[C@H:38]1[CH2:43][CH2:42][C@H:41]([N:44]([CH3:58])[S:45]([C:48]2[CH:53]=[CH:52][C:51]([C:54]([F:57])([F:56])[F:55])=[CH:50][CH:49]=2)(=[O:47])=[O:46])[CH2:40][CH2:39]1>C(Cl)Cl.[N+](C)([O-])=O.CCOC(C)=O.OS([O-])(=O)=O.[K+]>[CH3:7][O:6][C:4](=[O:5])[CH2:3][CH2:2][O:1][C@H:38]1[CH2:39][CH2:40][C@H:41]([N:44]([CH3:58])[S:45]([C:48]2[CH:53]=[CH:52][C:51]([C:54]([F:56])([F:55])[F:57])=[CH:50][CH:49]=2)(=[O:47])=[O:46])[CH2:42][CH2:43]1

참가 물질

9

반응물 4

HCID 67749Trifluoromethanesulfonic anhydrideHCID 685102,6-Di-tert-butylpyridine2회HCID 80252Propanoic acid, 3-hydroxy-, methyl esterHCID 178484845HCID 178484845, 화합물

생성물 1

HCID 178500919HCID 178500919, 화합물수율 95.7%

시약·촉매·용매 4

HCID 6344Dichloromethane용매HCID 6375Nitromethane용매HCID 8857Ethyl Acetate용매HCID 516920Potassium bisulfate용매

실험 절차

At 0° C. to a solution of 0.62 g (5.9 mmol) of methyl beta-hydroxypropionate in 4.5 mL of CH2Cl2 was added 1.4 mL (6.4 mmol, 2.4 eq) of 2,6-di-tert-butylpyridine, followed by 1.03 mL (6.2 mmol, 2.4 eq) of trifluoromethane sulfonic acid anhydride. The solution was stirred at that temperature for 2.5 h, was concentrated, and the residue was dissolved in 5 mL of nitromethane. To this solution 1 g (2.96 mmol) of trans-N-(4-hydroxy-cyclohexyl)-N-methyl-4-trifluoromethyl-benzenesulfonamide and 1.3 mL (5.9 mmol, 2.0 eq) of 2,6-di-tert-butylpyridine in 10 mL of nitromethane were added. The solution was stirred at 60° C. for 3 h, diluted with EtOAc and 1M KHSO4. The inorganic phase was extracted with EtOAc, the combined organic phases were washed with a saturated aqueous solution of NaHCO3, brine and were dried over Na2SO4 and evaporated. Column chromatography on silica gel with EtOAc/n-hexane 1:3 gave 1.2 g (95%) of trans-3-{4-[methyl-(4-trifluoromethyl-benzenesulfonyl)-amino]-cyclohexyloxy}-propionic acid methyl ester as light yellow oil, MS: 424 (MH+).

후처리

  1. concentrationwas concentrated
  2. dissolutionthe residue was dissolved in 5 mL of nitromethane
  3. stirringThe solution was stirred at 60° C. for 3 h
  4. extractionThe inorganic phase was extracted with EtOAc
  5. washthe combined organic phases were washed with a saturated aqueous solution of NaHCO3, brine
  6. dry with materialwere dried over Na2SO4
  7. customevaporated

출처 및 근거

ORD 기록
ord-0ab0dbe7d73b40679dc1f0b713d0a990
출처 데이터셋
uspto-grants-2005_11
특허 번호
US06965048B2

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